Unfortunately, Covid decided to change my plans, and I made the decision to hold off, in hindsight it was a huge mistake and no one could have imagined that property values could have increased at such a high rate.

Should I wait for Spring for greater inventory, or for lower rates to see if cashflow improves?

If it is someone you know you can give them a straight return as if its a loan - can provide a lower interest rate to provide upside - it really depends on the lender and what are they concerned with and what is their risk profile. 

As Vince said it is a quick guideline and won't work in most places with current interest rates and house prices. 

Paper where the current administration is focusing on.You own a property where, regardless of the interest rate, you get $250/m cash flow.

First thing I'd do is check comps to get an idea of the demand and rates you can charge for your condo as a MTR.

Down payment amount varies and more you put down the highre you will be in the queue of applicants, also down payment varies per your credit...Dodd Frank IS in play!!

Check their occupancy, nightly rate and amenities.

I've seen many investors get burned because they failed to understand their hard money loan terms/rates, even if they did acquire what should have been a home run deal. 

I've also held of holding properties in individual LLCs that are owned by one S corporation, which allows for a 60 / 40 split between ordinary income (regular tax) and dividends (capital gains tax rate).With the goal of minimizing taxation and liability protection, what would be the recommendation from more experienced people here?