They can fit between very tiny spots and will eat their way in.

Keep an eye of city ordinances on STR, the local government may get backlash from hotels if STR is eating into their business.

We've been fortunate, but from the seller perspective, it's risky as you can eat-up 2 months of holding costs, then have the deal fall apart, and you're back to where you started with no real recourse to the buyer except an appraisal cost.  

That's likely a significant profit eating decision.Also, is going to new AC systems going to increase your profitability vs leaving them with window units?

If they own a restaurant, do they charge you when you eat there?

@Kurtis Johnson hard money can be expensive and eat up your profits fast so you need to make sure you can find a property you can get and out of quickly.Also talk to several lenders.

Know that this is a dog eat dog industry.

Are you staying local so you can self-manage, or planning on property management which will eat into your cash flow?

@Christopher Olsen my hunch is that taxes would eat up most of your returns.

I think we can do this easily be eating at restaurants 1 less time per week.