However, the road block I face is getting to a point where I think it’s an “ok” deal (meaning it’s not fulfilling the 1% rule, but more like 0.75% and little to no immediate renovation cost/typically a new build townhome) and then I start to question whether I could find a BETTER deal if I just keep looking.

It's not hard to understand the disqualified party rules and prohibited transactions. 

I recently sold one I had on Seabrook Island because the club/regime/HOA were frequently changing the rules and making it harder to operate smoothly.

I would look for a 2 bedroom 2 bath duplex with a one car garage for each side located between the two units and each front porch on the each end of the building.  

I agree that the upside here is knowing most of the mechanicals need to be redone upfront, so there should be fewer ‘surprises’ along the way.Setting aside a solid contingency fund is a must—do you have a rule of thumb for that?

It's an amazing market to be in because you can still find the 1% rule and positive cash flow while getting amazing appreciation potential.

.- I prioritize building strong, professional relationships with my buyers by taking the time to understand their needs and goals.

And the changes, such as regulation, city development, traffic flow, building views etc happen very quickly. 

I just had to pay 11k for a new Hvac system on one of my buildings.

But I was lucky to get into the cabin building and I'm doing the same with the cabins that I did building my rental portfolio.