I also believe that I should also invest is my business.

.: Quote from @Chad Hale: I used QB when first starting my property management business.

This arrange that you will have will likely be a headache(major assumption on my part).First - Do not do business with a friend. 

A great lake front home doesn't have to cost a mint but it sounds like you want something that is really fantastic which will bring a higher nightly rate.

If millenial homeowners can't even change their home's air filters, or snake a toilet, or change the oil in their car, that's guaranteed future business for HVAC companies, plumbers, mechanics, and those places all need a place to conduct business in.The commercial mortgage pricing software I use has somewhere around 50 different asset classes in it.

I wanted to create an STR experience and bring my bold ideas to life.

To find reliable contractors, ask for recommendations from other investors, real estate agents, or your local hardware store, and check platforms like Angi or Thumbtack for reviews.It’s best to bring a contractor out after the inspection so you have all the details to discuss.

@Ella Marie, I can't speak on behalf of your market, but in my respective market, competition is tough, and the successful fix-and-flip vendors are often full-time operating businesses.

I don't disappear when things get hard.Luckily, the investor/seller agreed that adding a fence and some other things would bring the property a better sale price.Not all agents are experienced, and not all investors need an agent.   

For now, staying local allows me to leverage my property management experience—most of which came from working directly for family and close business associates who were property managers, contractors, and business owners.