We plan to keep them on a month to month lease but after a few months, have them sign a year lease and increase rent, however, we need help finding a GOOD app/website to get lease agreements/documents from or get a template so we can fill/add certain things we want.

I am not yet familiar with the management fees for an STR yet as we self manage, however Cleveland itself is currently STR friendly and just requires them to be registered if you have stays over 90 days and then you register with the city and pay $35.

Quote from @Andrew Steffens: I have no idea who that is hahaI have seen an increase in this (like everyone else) because Airbnb spoils guests. 

in a stick frame market and one of the cheapest markets to build we build with margin at $190 or so a square foot. that will go up over time about 5% or 10% a year to keep up with new build price increases. we are buidling a 3 story walk up and source some of the lowest priced crews.

But, the self-sufficiency test for FHA loans can be really difficult in SF, meaning that the market rent from units you will not occupy must be sufficient to pay for the mortgage payment. 

They’re “meaner” than me so they charge late fees (I get 1/2), file pay or quits, and increase rents faster and further than I would.

We have an existing mortgage (backed by these 2 lots and 2 others) and given the increase in appraised value there is no need to pay anything back to the lender when selling the lot.

Upon BP member recommendations, my husband got his real estate license which now helps increase our access and decrease our transaction costs.

.- The new PMC you want to hire will have to increase your Placement Fee, so they can offer a commission to an agent that brings then a tenant.

So, I would work to increase your knowledge and experience and really identify a strategy that suits you before moving forward with anything. 2.