I absolutely respect the fact that your tenant wants to maintain the quality of your home :) I do however think that these items are resolved at move out. 

get the other side rented out properly, with proper contracts, then also properly maintain seperate accounts for the rental income and expenses and bookkeep properly. stay firm but friendly as a landlord

The idea behind it, is that if the community is not structured correctly, these are all things that lead to the property not being maintained correctly, or the hoa owes some people money and that leads to assessments, which leads to you not being able to afford to pay your mortgage. 

A question that may have been come up many times before but I will ask it anyway, what’s the best strategy to be considered as RE professional for tax purposes while maintaining a full time W2 income.

use capital from banks at 5%.Stage 3) maintain 100+ properties and replace some of the SFR with   multi-unit apartments using all debt.  

Do you charge for monitoring and maintaining vacant units?

I only see opportunity, especially when the house was so well maintained.

I saw this as a positive indicator that the renter is invested in maintaining the condition of the property.How did you find this deal and how did you negotiate it?

I've decided to be more disciplined with the money I make from teaching and believe I can consistently maintain a $300 budget every month just for wholesaling.

We have kicked around the idea of maintaining two properties and become snowbirds but it hardly seems worth the expense of having a home sit empty for 8+ months especially in NY.