Refinanced August 2020 into a 15 year loan at 3.375%

Your realtor will be able to give you a much more detailed market specific answer but with house hacking and a VA loan it should be possible to get 0 out of pocket.

Since the original loan was apparently for a primary residence an LLC could never qualify because it isn't a person who would owner occupy the property. 2.

I forget It was likely a mix of private and traditional loans I just don't recall to be honest nothing illegal. 

I own a mortgage company, so I have my loan officers use this Fannie Mae income calculation tool for all business for self borrowers: https://singlefamily.fanniemae.com/applications-technology/income-calculator .

I would certainly disclose the currently approved special assessments, but since any further financial obligations and project plans have not been voted on by the membership, approved in a budget, or secured in a loan; must I disclose the knowledge that the board is trending in that direction?

If you're using a DSCR loan to purchase the home, most lenders use the lower of the lease agreement or 100% of the market rent from the appraisal form 1007 to determine the DSCR.

A rental market analysis can reveal demand trends​.Secure Financing: Lenders offers tailored loan programs for multi-family, mixed-use, or fix-and-flip projects.

So for the first property which will cost over $1 mil to construct, there will be stacked loans, essentially $280K will come from loan assistance program,( the name is not correct but the same idea).

If you need any help with the financing, Aslan is beginning to offer the Chattel loan very soon which could be a great help.