Business-related payments sent as “personal” (which would be a violation of PayPal/Venmo/CashApp terms, btw) DO require 1099s.I do not have my contractors’ SSNs – what do I do?

Many banks securitize their loans (bundle them together) and sell the loans to Fannie Mae or Freddie Mac, while continuing to service the loans, that is collect your payment.

If the loan was fully funded at closing and since then the loan is in an interest-only payment period, these numbers would equal. 

I have 9 loans currently so looking to do a conventional loan on my next depending on that process.

While I don’t own investments there, I’ve explored the market and see potential for some long-term growth.

. $300sqft to build at least.If you have any sort of mortgage on the property you will need an attorney to handle the mountain of paperwork the bank will give you for a lien release. 10k+, also probably some nightmare terms to have to build and sell immediately and god knows what.At this point a year has passed and you have spent at least $60,000 cash, you're about to break ground on a structure that will cost you at the very least $400,000 to build, you are still 1 year away from cashing out because you have to now build a house.

House hack another property with a low down payment loan and use the remainder or the proceeds to either renovate or purchase another investment property?  

When your LLC takes a loan, expect as members to personally guarantee the debt.

I have a couple of investments and am about to jump into a Short term rental while still being a w-2 employee.

If it has any basis at all (such as you left the apartment during your lease term for what you felt was a justifiable reason and stopped paying rent, but the landlord disagreed) then you may be better off paying a rather small settlement.