They have never missed a payment to me and I am currently invested with them. 

And then, with every new program manager we get it seems there is a new idea about what color scheme will be better to keep the clients calm so we repaint them walls at least with each New management change that occurs.

Quote from @Gideon Mukoro: Landlords, property managers, and tenant screeners—how often do you encounter fraudulent income documents (bank statements, paystubs, etc.)?

Hello,I am a real estate investor located to Southeast MA, I own and manage a small portfolio of 23 units and am looking to expand and scale out of state as the returns and market have been quite difficult in my area: due to CAP Rates, specific building class I am looking to invest in, and rising interest rates/minimal inventory, as well as it would be nicer to be diversified and in a more landlord friendly state.  

I've purchased a couple of my investment properties directly from property management clients who decided to sell. 

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

Quote from @Obed Calixte: There are a ton of free tenant applications online and through property management software companies such as turbotenant, rentspree, zillow etc.You will want your application to meet any state specific guidelines (if applicable). 

I’d recommend starting by connecting with local investor groups and networking with other professionals in the area.Also, seek out teams that are actively investing and managing properties on the ground.

He get's principal and simple interest payments over a number of years.I'll manage the deal and the property.Looking to create a proforma for this that would fit a typical rental analysis but insert the detail of having private money cover the DP.

If they’re open to living elsewhere, keeping the property as a short-term rental seems like the more profitable long-term play.If you’re enjoying the self-management and the demand remains strong, I’d lean toward keeping this property as an STR and exploring ways to add another.