I don't want to be caught in analysis paralysis, but a few more months of saving the way I have, would help me sleep better at night, when I buy my first investment.

Although some guests do want to come in and unplug and relax for a couple of nights at least in my location where the big draw is hiking and skiing at the end of the day my guests wanted to go to the brew pub and eat and drink local beers then walk back and sleep before going out and doing it again the next day!

Sleep Bee just opened up there and that is one of my favorite brunch spots.

I think we had 6-8 offers going at one time. my wife and I saw numbers in our sleep at that point.

These sleep 8 and are on the Carribbean, penthouse level, older units.

my five bedroom beach house can only sleep 14 people). 

It sounds like you will be able to do it with low risk which will help you sleep at night and cashflow great! 

A 250K building your net worth should be 1 M, this is to sleep well.

It will cost you less in the long run and you will be able to sleep at night.

Perhaps you will miss out on levered wealth accumulation, but you will sleep well at night.