The reason the shower is being replaced is because they notified me of a water leak coming from the shower.

Newer roof (2019) and newer water heaters and HVAC.

If you are taking extensive time managing, spending money on gas, repairs and maintenance you are under water.

They left us without hot water for two months upon moving in.

We could sell that house by itself, but it would be sold under a land in common agreement and an HOA would need to be formed.I also confirmed with the Public Works department that a 2nd driveway can go in, with a septic designer that there's room for second septic tank, and with the public water company that they can tap into the main water line from one of the neighboring roads.I'm sure there are some more details that I would need to iron out that the code officer didn't bring up, but the high level answer I was looking for is that my town does allow selling off a second house under the LD 2003 legislation.

The 2 main issues are that there's a leak in one of the bathrooms that is causing water to flow under the sub-floor and into the crawlspace. 

All of these are possibilities, and all have their upsides and downsides.But, at the end of the day, if you are thinking of this purely as an investment, particularly passively, it is not the highest yielding investment.  

If there are excess funds after paying the local/school real estate tax bill, the remainder can go to:Current real estate taxesCurrent Muncipal liens for water/sewer or any other bill initiated by the municipalityState Liens, usually for outstanding state taxes, sometimes employee/employer taxesPA State Inheritance Tax which applies to all deceased owners and starts at dollar one with no exemptions, unlike the Federal Estate Tax. 

You can close in the business name/LLC here.You are not required to have your investment property in the business name, however, some lenders and bank may require it if they are a purely business purpose, lending institution who servicing companies, mandate commercial purpose only.And yes, finally you can get landlord insurance.I recommend shopping around and comparing a few quotes to get started happy to connect to talk further strategy and detail.

Most recently, I worked with a client out here in Colorado that let their parade of homes house (from 25 years ago) in a gated community literally fall to pieces; mold between window panes, water infiltrating the kitchen due to lack of roof repair, patio pavers crumbling apart, downspout misplacements that caused water infiltration into the living room....just a mess.