Newbies create a lot of different issues, however.You are probably not going to be able to use Fannie Mae as a contingency.

If the house doesn't pass the occupancy inspection before closing, the municipality can usually issue a temporary occupancy permit.

Some part of these neighborhoods change drastically, but the main issue is the amount of supply.

There are a lot of market-specific issues you'll have to grapple with and also, there are plenty of landmines in MFR on its own in CT that you'll have to be ready for, in addition to the nuances and complexities of developing something like this.

Here in TN we issue POQ within a couple of days of rent being overdue, usually giving them 14 days to correct before official eviction proceedings start.

Had some issues connecting VRBO at first, too.  

Our primary issue on both previous CPAs was lack of engagement/enthusiasm in their work.  

I tend to agree and don't think it will be an issue.

You've got ADA, FHA, and the Oregon Department of Agriculture issues. 

Other advice, especially that pertaining to tax benefits, is also highly appreciated!