You get built in property management which makes dealing with repairs easier. 

The plumber’s report indicates that the leak may have been caused by an overflowing tub or sink upstairs, but the tenant in that bedroom denies any such incident.As a result, I now have substantial expenses for the plumber and restoration company, including drywall repairs, painting, texturing, and reinstalling electricals.

Yes, if you are confident in your numbers....particularly the repair/reno numbers. $20k is not much and will be eaten up real quick.

I haven't reviewed the Standard Lease Agreement yet, but all I need is the right to sublet, and possibly some negotiated capital responsibilities (owner pays for repairs over a certain amount or split responsibilities on certain expenses).

We take pictures on a pre-inspection only of existing damage, which generally doesn't exist because we repair anything that happens between tenants.

Focus on building a network of contractors for repairs, set clear boundaries for house hacking, and take advantage of tax benefits.

(My contractor often just answers these calls and makes the necessary repairs without me ever knowing).

Your loan may also be capped at 65 or 70% of the after repair value.

He started with me just after retirement and I recommend you look for a handyman who is retired because they are typically less expensive and as my guy likes to say, every day is a Saturday and that means they can get repairs done quickly.

I usually suck up all the plumbing issues with LTR because I know it will just waste my time and of course plumbing is the most expensive repair every single time.