There is just a specific established number based on those comps....and while we're at it, that 1% rule is BS too.

Right now, my whole roof needs to be replaced due to age and small leakage. 

The loan to value is no where near as high with conventional and units, so either go with a single family and rent out rooms or just continue moving until you've acquired a few more properties using owner occupied money (it's cheaper).Then, once you're established in your job and know where you're going to settle, buy the be all to end all house.Stephanie

You could then repurchase and establish a higher basis, so you are not paying taxes on that piece of gain later. 

Big picture though I do think rates should increase next year, especially for established, well-reviewed properties.

Fixing things that break aka maintenance and also replacing things that are at end of life like a roof replacement also called cap ex (capital expenditures).

I'm searching for someone who is more established than the people listed on Thumbtack, Home Advisor, etc. because I feel these sites tend to have contractors who are a little more flaky (but you really can get lucky and find great people there too)!

Depending on how old the roof is on the property you could look into Citizens.

On the rental we have a 4k dollar bathroom remodal happening this month that we owe about 2.5k out of our own money (not rental) and just today the renter emailed us about a leaky roof.

Establish your vetting process and how you will find finding tenants (i.e, credit criteria, referrals etc. and zillow, realtor.com, MLS, etc.)2.