Some states like california you can do trust deeds where you break off the loan into multiple pieces.All of these will require significant capital to scale with your own funds. 

Assuming you have another stream of income when you move there and I hope you do, I would recommend using the smallest amount of capital possible and invest in the most doors (1-4 units) that you can. 

You and this private person you met hammer out the details of the loan at the kitchen table so to speak and you seal it with a handshake and your reputation that this Private Person already respects or whomever introduced has vouched for you.But if a man opens a lending company tomorrow with 50 Million of his own capital and he checks in on the HML market to see what it bears and he copies his products and UW guidelines and now is he PML or HML? 

.: Emotionally..... pay off your primary.Financially..... use the $$ to buy assets that make you $$...hands down a smarter use of your capital Especially if your interest rate is well below what the current rates have been. 

Living in the property for two years likely allowed you to claim the capital gains exclusion... up to $250K for singles or $500K if married.

First you need to learn to separate the following:Maintenance: usually things related to wear & tear or tenant damage.Repairs: usually broken items like doors & windows, caused by tenant or nature.Capital Improvements: usually expensive things that wear out: hot water tanks, furnaces, roofs, etc.The seller is correct that Repairs & Capital Improvement items should not be a factor for awhile (ALWAYS get your own inspection to confirm).

In 2021 we bought the building for $1.5M using private lenders, pushed the occupancy from 50% to 80% occupancy and it appraised for $3.125M, allowing us to pay back the private mortgage.Right now, we are in the predevelopment process of design and piecing together the capital stack for the redevelopment deal, which will be made up of historic tax credit equity, RestoreNY Grant, DRI Grant, etc.

I had capital and employment and properties from the start.

If so, you can't really pivot to short-term rentals there and have to capitalize on the inn vibe and in-house services.My major question is why is the current owner, who bought it after it sat vacant for twenty years, looking to sell you the problem they can't fix?

While the offer sounds tempting, I want to ensure I capitalize on these contracts fairly and effectively.Here are my main questions:Should I entertain the idea of terminating my current contracts, or is it better to stick to my original wholesale plan?