I had a similar situation with a neighbor that constantly caused issues.

This means I am constantly researching different sub-markets in the D.C. area to try and find the best locations for future growth as our fund looks to buy and hold our investments as do many of my clients. 

MTRs can offer a nice balance between the steady income of long-term rentals and the high cash flow of STRs without the constant turnover.In terms of locations, I've noticed that areas close to hospitals or corporate hubs tend to do well since travel nurses and professionals on temporary assignments often seek out these rentals.

We initially started with Podio, but found ourselves constantly needing to hire a developer for new adjustments.

If you ask a seasoned investor if they say they know it all they are full of it - you are constantly learning and there are always new situations that people go through that others can use as a learning experience

I understand the tension of customers not wanting to constantly give everything up front for fear of the contractor having no incentive to work quickly, and even worse the possibility of them running off with the cash...but in the same breath the contractor wants to be certain that the customer is in fact going to pay, and pay in a timely manner.

Remember, no system is perfect, so avoid the temptation of constantly chasing after the next shiny object.

Like many (most) businesses it requires an investment of capital; money expenditure for ongoing marketing; management of operating, marketing and professional personnel; keeping accounting records and filing tax returns; established sales practices; constant monitoring of goals, budgets, and productivity; establishment and implementation of operational systems; and providing customer service.  

I am constantly surprised by all the reasons people seek out midterm stays and, really, you're only limited by your creativity.

I made it easy for potential investors to see themselves working with me by constantly giving away free content.Giving talks and writing a book (not yet published) were also big parts of building my thought leadership brand.