But if I keep pushing it off until I feel "comfortable" it will never happen.

@James WilliamsWell if you are comfortable with it go find a hard money lender in the area.

See if you can find larger ones with higher room counts, where you could convert things like dining rooms into bedrooms.

A lot of folks are comfortable with anything more than a year because that represents two tax years and two tax filings. 

I originally looked locally & then realized the big money makers in STR are down south - best decision I ever made was pushing myself out of my comfort zone re: long distance investing!

Best answer is whoever you feel most comfortable keeping as a tenant.

I think if I was further down the line and more comfortable with an area/the process/my numbers game then I might average it out/compensate the cash flow over other deals and put the extra back in the process.

I am much more comfortable learning the ropes and doing a deal with only 30k invested.

We like that syndication allows for one or two people to act as GPs and take ownership over projects, but have found the intricacies of it to be super complex, and are concerned that the potential investors in our network might not be comfortable with it....so basically, we're still trying to sort through all of that!

To live within our means but comfortably till then.