Maybe someone with experience with that will chime in.Of course, STR (short term rentals like AirBNB are taking the "vacation" rental industry to whole new levels. 

Is anyone gracious enough to give me some tips on where to start.

Currently, we are leasing the property, generating a net profit of $380 per month and living in Missouri.We are contemplating the decision to sell this property and potentially gain $239-278K payment to buy additional investment properties in Missouri given the rising rental rates in the area, we anticipate increasing our rent and potentially securing a net monthly profit of $780 (annual$9,360).While we acknowledge a monthly profit, our concern stems from the apprehension that the property might not fetch as high a price in the next five years or that our HOA fees and taxes could escalate.Given this situation, what course of action would you recommend?

It depends, of course, on what your goals are.

Even when things go off the rails, you should have a provision for unexpected expenses factored into your budget.At a certain point of investing more and more money into the project, you’ll want to understand that you may need to course correct or even, in extreme cases, pull the plug and seek a quick exit and not give into the sunk cost fallacy.

At this point, I knew we were going to be screwed as the listing agent was for sure going to be showing his other scheduled showings the following day on MLK Day (even though he said he wasn't going to and gave us his word).Monday comes around, and of course, the listing agent says they jumped the gun on accepting the offer, and wanted to see what else they could get as an offer.

Now many great hotel investors and operators started out running their first hotel however thats probably not the course I would take.  

Robbie, Local to you CPA/PFS in Bryn Mawr we should talk shop and of course check BP Tax Finder and posts lots of great practitioners on BP.  

Of course, we are going to get a vacation home loan.

I didn't know where to start or where to look or whom to turn to I was lost with no one to turn to and they were the first ones to give me a false hope of support, before I found this company of course I couldn't get no kind of support from anyone, but I am realizing now that you are completely correct and they're not going to help me in any sort of way and I need to move on to try and find another way of getting some kind of support in my choice of doing this but thank you for your honest opinion and if you have any other suggestions or anything you think might help me on my journey I'd be happy to listen.