The more you study and research your niche, the higher your confidence will grow in your purchases and the uncertainty will be out the window!

@Mike Roy - You're too kind to label me an "expert" though I've certainly put my study time in. 

A corner unit slightly smaller than mine that was not renovated closed for $405,000 in March 2019 and there is a pending 1 bedroom slightly larger (has a small study and larger bathroom) at $439,000 which will be closing 7/31 so I will be able to see the sale price soon.

I bought $135,000 pair of Townhomes that grosses around 60,000 per year. you need to study the area to see what similar short term rentals are grossing.

study for your real estate license .. do leasing if you have to.. work on a team.

I have a few more months in the military so I was using the next to few months to study this stuff in and out.

I also worked part time last year as I was studying for a masters degree.The issue is we need the profits we will make from the sale of the property we have on the market to use as part of our down payment for the next one.

Denverinvestmentrealestate.com has a bunch of case studies on the subject as well. 

I have done my studying and will continue to study everyday but I don’t want to get stuck in analysis paralysis. 

If you dont have an agent, this is probably a case study in why you should get one thats knowledgeable on your market.