-you mention that the house is newer, and therefore should require less $ to maintain.

Both of these options (selling or raising rents) will benefit you - it is truly up to you on what would make the most sense - raising rents will definitely drive up your cash-on-cash return on a monthly basis but selling would also allow you to acquire a large sum of money that can be used for new construction so that you can maintain your current reserves.

We don't trust people with operating the fireplace and think the pool will be a hassle to maintain and a drain on revenue. 

You do everything in the LLC name, you want to maintain the separation between LLC and personal.

I believe it is going to be very out dated but maintained enough for the house to be livable. 

Purchase price: $103,000 Cash invested: $25,000 Great, well-maintained single family house with a long term section 8 tenant that takes pride in their residence.

The property manager will have a better read on ability to place tenants, do tenants tend to stick around long-term in the neighborhood based on type of property it is, rents (and future projections), structuring the lease, and executing the long-term strategy of maintaining the asset, etc.

I still have trouble wrapping my mind around this partnership carrying more risk than being the sole maintainer of a property.

I don’t have enough repairs/maintenance to even maintain a relationship with a handyman/GC.

There are also additional costs of operating and maintaining an LLC, like separate bank accounts, annual report filings, tax filings, etc.2.