We have a decent plan working now, its just a matter of financing and scaling.

It’s great that you’re cash flow positive and planning your next move.

However, are you planning to do a 1031 exchange, or is this a primary residence? 

Like @Collin Hays said, it is being driven more by neighbors tired of poor STR owners not keeping things sorted.We only look for places in vacation areas with a long history of owner driven STRs vs big cities and the like.

If you're working on other projects during that time, it could create an issue, as it would for any employer.Why not be upfront with your boss and let them know you're planning to get your real estate license?

I also am planning to meet with my PM on Monday to discuss pain points and better expectations, I would love to hear what sort of expectations you set with property managers?

I use Beyond pricing in my vacation rental markets and Pricelabs in my city/mid-term rental markets.

@Jordan Meltzer unless you find a screaming deal - a Class A property won't cashflow for 3-5 years.Class B: 1-3 years.Class C: most investors don't properly understand the risks, so should stay away from them.So, you may need to deal with negative cashflow, but plan on appreciation increasing your wealth.

We never planned to keep our new build for 30 years, which is why we would have never used your cap ex valuation. 

One of the cool connections I've made is with someone that has over a million subscribers to his YouTube channel that is now working with me to take my channel to the next level.Proverbs 15:22 teaches, "Plans fail for lack of counsel, but with many advisers they succeed."