Don't get me wrong I love the software, but I have one tenant, it's one condo, can't I just hand over a simple spreadsheet with all necessary tax documents to my accountant and call it a day?

We have been past our "Number" for several years, so expanding into this Economic market we weighed more towards Risk Analysis and Wealth Preservation than bigger numbers (debt/asset growth) and increased exposure.

How much will it increase your expenses?

Structural (brick) changes/repairs could increase these costs.Knob and Tube Rewiring: Rewiring a house to replace knob and tube wiring is indeed costly, particularly for a complete job.

Would love to team up and increase value of such cooperation.

It is easy to start simple and go more complex as needed. 

And if you have the budget for it, I recommend furnishing the rental because it will increase the income you can make on it.

I’m having the darnest time finding a simple handyman. the prices that the contractor gives me is such a rough estimate lol they haven’t even asked me for measurements or whatever. 10k for a click vinyl floor?

A late fee is basically an increase in rent:) Regarding renewing the lease, would carefully go over the payment history to determine the risk.

Your mentor has needs; try to meet them and develop a mutually beneficial relationship.A mentor can be very beneficial to your growth, but it's not as simple as one post on a forum full of strangers.