I recommend talking to a few commercial lenders in your area that you'd like to work with (prioritize the smaller banks, you'll get better service) and ask them in advance what their criteria is for debt service coverage ratio and the percentages they use in their underwriting for vacancy, reserves, management, etc and how much flexibility there is in those numbers.

My full time business is quite flexible still, so I'm confident I'll be able to juggle both. 

The people selling the building are friends and (maybe) willing to be pretty flexible as long as they get the money they want.

Like you, I can be a big flexible with a previously good tenant. 

With a HE I should be able to get 70-80% back, and it’s more flexible - you only HAVE to pay interest, but can pay off sooner by choosing how much to pay back each month.

Second question: Most of what I am reading in the forums (again, a bit of a generalization) seems to favor HELOCs over Home Equity Loans, mostly for the flexibility that a HELOC offers since you can tap into the money whenever you want.

However, I do plan to work with the surveyor to put a TPM on the units and include it in the plan for zoning approval, therefore we have the flexibility to convert them to condos down the road.Possible exit strategies:- Option A: Entitle + sell the entitlement right to the next developer- Option B: Entitle + partner with local builder/developer to build the project.I understand every market is different, but love to hear folk's opinion on what are possible things I should pay more attention to.

They tend to be more "flexible" with your Real Estate intentions and don't pressure you into generating sales.

I am a part-time agent who works full-time as a Property Manager, so I do have lots of flexibility to do what I need to do during business hours. 

Also, if you add a financing clause to your purchase offer then it should give you more flexibility as far as having time to shop around for a good loan (Verify with your agent, laws differ across states).