I would then plan to use this forced equity (since I plan to buy a fixer upper) to invest in another home.I have been constantly reading to househack right into the MFH, but this may take some time for me to acquire the money and purchasing power.

That’s usually a sign of being in a management-heavy neighborhood and at least in Buffalo, low opportunity for forced appreciation.

I would then plan to use this forced equity (since I plan to buy a fixer upper) to invest in another home.I have been constantly reading to househack right into the MFH, but this may take some time for me to acquire the money and purchasing power.

Using your VA loan benefit is another great way to get started in real estate investing.I’m active duty Air Force with four properties.

However, health concerns forced me to step away from the hustle about 6 years ago.Fast forward to today, I'm officially retired and living in sunny California with a renewed sense of energy (and much better health!).

You can only prorate the primary residence exclusion in cases where health or a job transfer have forced you to move.

You bought 60 to 100 year-old properties primarily for cash flow and now you feel your investment is not working because you are forced to re-invest some of your cash flow back into the properties.Here is the thing: they are your assets and you can make them better and more valuable.

So only forced sellers are going to sell, as everybody knows that tourists are going to be back with a vengeance.2.

Please be gentle; I'm new at this and it's pretty complex :)Structure / Legal Details- we'd establish market value through a combination of comps from local real estate agent and an appraisal- attorney would establish all required "arms length" aspects including a mortgage at a minimum standard federal rate- LLC would pay us back based on a standard promissory note over 30 yrs Pros of selling to the LLC (I think)- A sale now would be the only time we'd be able to take advantage of the cap gains exclusion on this house bc we won't qualify for the "live there 3 of 5 years" rule due to the timing of our lease and our last time of residence. 

Because if "over priced" the market decides that, and will reject your product/service, and simply not purchase it, forcing you to discount.