If there have been donations for technology upgrades...
Is it possible for someone to ask an abbott exactly what he wants donated funds to be used for? To ask the what specific items he could use?
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Quoting from The Bhikkhus' Rules A Guide for Laypeople
Appendix D: Examples of Vinaya Practice
This appendix illustrates how the bhikkhu's rules are actually practiced in different monasteries and communities. Each example is taken from the community's own guide or from devotees' experience.
(1) AUSTRALIA: BODHINYANA MONASTERY
One can also make an invitation, 'pavarana,' to cover any circumstances that you might not be aware of — a health problem, need for a toothbrush, etc., by saying, "Bhante, if you are in need of any medicine or requisites, please let me know." To avoid misunderstanding it is better to be quite specific, such as — "Bhante, if you need any more food...," "If you need a new pair of sandals..." Unless specified an invitation can only be accepted for up to four months after which time it lapses unless renewed. Specifying the time limit, or giving some indication of the scope of the offering is good, in order to prevent misunderstanding — so that, for instance, when you are intending to offer some fruit juice, the bhikkhu doesn't get the impression you want to buy a washing machine for the monastery!...
In practical terms, monasteries are financially controlled by lay stewards, who then make open invitation for the Sangha to ask for what they need, under the direction of the Abbot. So junior monks even have to ask an appointed agent (generally a senior bhikkhu or abbot) if they may take up the steward's offer — to pay for dental treatment, obtain footwear or medicines, for example. This means that as far as is reasonably possible, the donations that are given to the stewards to support the Sangha are not wasted on unnecessary whims.
If a lay person wishes to give to a particular bhikkhu, but is uncertain of what he needs, he should make invitation. Any financial donations should not be made to 'X Bhikkhu' but to the stewards of the monastery, perhaps mentioning if it's for a particular item or for the needs of a certain bhikkhu. For items such as traveling expenses, money can be given to an accompanying anagarika (dressed in white) or accompanying lay person, who can buy tickets, drinks for the journey, or anything else that the bhikkhu may need at that time. It is quite a good training for a lay person to actually consider what items are necessary, and offer those rather than money...
So I get the impression that,
The Vegetation section says that a monk can't dig nor command someone else to dig, but ...
It is, however, allowable for monks to hint to laypeople or novices about what needs doing as long as the words or gestures fall short of a command. When bhikkhus need paths to be cleared, necessary work done on the ground, firebreaks made, etc., any lay attendant wanting to help should listen out for hints and indications: 'A post hole dug over there would be useful'; 'make this ground allowable,' etc. What is needed can then be clarified.
I don't know; that's only what I've read.
I try to avoid telling monks how I think they ought to behave -- more specifically I'll share with them what the rules of this site are, but I don't think it's my place to interpret their vinaya for them.
This is one of several questions on this site which ask what monks are allowed to do, I can't say I understand the motive for asking, so I feel it's difficult to understand what's really being asked.
You wrote that he replied,
"I could use some of my technology upgraded to teach online" upon being asked if he needed anything
I'm not sure what else you expected, "upon being asked". You could perhaps be happy to be told what someone needs, then you don't have to guess.