How much will be the interest rate, and terms of the loan. 

Normal mortgage rates are in the high 6's now, for a personal residence, and higher for an investment property. 

Quote from @Jonathan Chan: What kind of rates are you getting on gap?

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

Building a rental portfolio that replaces your income takes years and a lot of effort, this is especially true in our high price high interest rate market.You need to have at least a 10 year vision when buying real estate.

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.

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. 

Are the units rented at market rate, or is there room for rent increases?

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?

It's objectively rated as a great place to live, but obviously you need to be ok with Winter.