I will send you my calendar link shortly so that I can share the data with you live :)

He listed both apartments by himself, and as soon as the tenants moved in, they stopped paying rent shortly after. 

It is also very inconvenient for you to manage one guest putting utilities in their name then within a short time frame having to make sure all of those utilities get switched over to the new guest.

For illustration purposes, the windows are a 4 week lead time so you put the window order on your card and once they are installed, your lender releases the funds and you pay down the cards.I see too many “Gurus” teaching new investors how to use credit cards to cover down payments and they teach this because it creates the false perception that anyone can buy real estate with or without savings.

We are located in the Pittsburgh area, so we would prefer to set up our first short term rental arbitrage nearby, but we are open to exploring good opportunities elsewhere.  

Look at your monthly payment (PITI = Principal,Interest, Taxes, Insurance) + HOA + (other maintenance fees if any) and if this amount is less than what you charge for rent (whether its Long, Mid, or Short Term rentals) and you are happy with the positive cash flow, then yes.Or maybe you're breaking even with the condo but you have  knowledge that the condo will explode in value due to some business/attraction/law/policy that will prop-up the sales price in the near future, then yes.Really, it boils down to what your goals are for this first investment.

My idea is to build a mini village with modern cabins, but I'm unsure about its demand, worthiness as an investment, and associated risks.Here are some specifics:Investment Capital: I have $500K of my own and access to an additional $1 million from investors.Location: New Jersey, where I currently reside.Investment Goals: My primary goal is to generate cash flow through short term rental.Project Idea: I'm considering building a mini village with modern cabins.I would greatly appreciate insights from experienced professionals in the community on the following:Demand: Do you think a mini village with modern cabins would be in demand in the New Jersey area?

Andre - For starters I would recommend you read "Short Term Rental, Long Term Wealth" by Avery Carl;   You can find that book right here on BiggerPockets. 

I am licensed real estate agent but concentrated on investing and building a lead generation business.

This will likely determine whether short/mid/long term rentals are favorable in that specific area. 5) there’s so many things!