Every insurance company is different and each one beats to their own drum.Most are deterred by open claims, some aren’t.I’d really be careful about filing claims often.

A lot of the other duplexes and triplexes in the area have shingles and a lot of them have metal roofs so as far as getting renters neither one will really deter anyone.

Hi Laura,I personally prefer to live in house with no trees blocking it's view from the front yard, but a lot of people (as you can see from the posts) like trees in the yard (some like the house almost totally obfuscated and will plant even more).So if it were mine, I'd leave the trees for that reason, and just darken the shutters to a dark chocolate color, leave the paint as is (if it's in average condition), leave the fake well because it seems to match the structure and not detract from it (if new owners don't like it they can remove it easily) and take the shrubs down to foundation height to make the house look bigger.But if I were living there myself, those trees would be firewood for that fireplace (something your Realtor could point out to prospective buyers).

Second I would ask my parents what the prospects of living at home for some time. 

Yes hire a pro, the photos generate more prospects, and result in shorter turn around times.. contribute to higher rents. top down views actually decrease the showings, especially if room sizes are given..

I had prospective tenant's view an apartment yesterday.

Sit back and let others find prospective deals and send them your way.

If the prospective tenant has a good track record for doing this Airbnb thing you speak of, go forth with this venture.If he has no experience, it is a trainwreck waiting to happen, and I have 23 STRs in this town.  82 beds, 37 bathrooms. 

@Michael Hawrylak while you are paying off debt and building cash reserves, it would be a great time to identify a target area and begin prospecting and assign some deals.

If they have more than six months remaining on their lease, I tell them they can pay me an early termination fee equal to two months rent, stay responsible for rent and utilities for a full 30 days (whether they occupy or not), and allow me to market the unit and show it to prospective renters.