Beyond that, if it's a multi family, make sure you understand if there is a common utility service you need to put your name on so there is no service disruption. 

I didn't know about conventional not counting boarder income for non-serviced properties.

I run a small nature hotel (luxury glamping) that offers similar services to bed and breakfasts.

From our conversation, it seems like there are indeed properties that will cash flow in the 6-8% Cap rate and 10%+ cash on cash rate and that there are Debt-Service Coverage Ratio (DSCR) loans around 5.5% and 25% down that will fund a purchase with the appropriate cash flow. 

Your tenant is avoiding service to avoid starting he process. 

Mitigation Strategy: Cost-efficiency improvements such as energy-saving upgrades or negotiating better service contracts to reduce operating expenses.

After finally getting into Hostaway, I felt it wasn't for me and the customer service was not very prompt or helpful with the issues.

I would expect to see property management, admin, marketing, and contract services (more than just lawn care.) 

You want the services of a reputable cost seg firm.

Mail them the documents or use some online service like DocuSign