Measuring if a property is a reasonable first, second or last investment is not a function of how much you have saved.

This might offer more security but also could complicate tax reporting.Taxation of Y as an S Corp:If Y is profitable, electing S Corp status could reduce self-employment taxes, but it also comes with more stringent IRS rules.

Some items to be aware of include, but not limited to:  zoning in County may conflict with the City, utilities that belong to the City infrastructure may require that you annex the property prior to rezoning or other entitlement, County development standards may be different or less stringent than City standards which would cause the development to be non-compliant when annexed.I would echo the same as Bryant Brislin, you will definitely want to connect with someone that can navigate this process for you. 

If they don't pay the dues the HOA can lien the property or enforce measures on it. 

That's an imperfect measure, but we really need to get a sense for what you have to do in order to GET that $108k that it currently brings in.Not giving you the yes/no on if it's a good deal or not, just giving you some ways to think about it. 

The rules are stringent as well. 

@Alec Jacobs We typically m aside the windows and buy our own and usually get a quote based on the measurements from both the box stores and an independent glass company.

is there a device i can use to measure the level of pander?)

Answer that and then measure this decision against your goals. 

First, it's a plan-z measure, that if they have to take the asset back, that after all the expenses of such and what-not, there potential losses are mitigated to $0 or as close to $0 as possible.