I am a real estate agent and I work with multiple investors here from out of state. 

They can advise you on the specific rules and regulations that apply to your situation and help you maximize your deductions while staying compliant with tax laws.

For your situation from what it sounds like, it is probably more advisable to go the multi family route.

Maybe, this would be considered a distribution of property from the LLC which would cause a taxable gain should the llc not have sufficient basis to take from.For #3 and for all of your questions really, there can be a lot of hidden complexities depending on your exact situation.

I'm a software developer and very good with a spreadsheet and all, but I'm wondering if I could secure an experienced lender who not only can lend, but also provide advice on a deal like this from having financed similar situations before.Pointers to financial calculators for such an endevour and hotel/motel renovation-style lenders & contacts appreciated.Thanks,Matthew

I don't like the idea of taking advantage of anyone, but personally if I found an opportunity like this I would understand the reality of the situation is that if you are able to make a favorable deal, so can anyone else in the market, so might as well strike first and be more reasonable during the turnover process so you can sleep well at night. 

My parents deal with owner occ and those have been busy, multiple offers on many properties

They should be able to help you strategize what will work given your current situation and qualify you appropriately. 

OK here is my situation, I'm 26 years old with $90k I'm willing to start investing in real estate with, I have zero debt and near perfect credit history and not much liabilities in life at this point......no house, still single, no kids etc.

I’m seeking advice from this group regarding a situation with our primary residence purchased in 2021.