Its a condo with a HOA.

A 1/1 condo that's been in the market for a while drops to 100k with 350ish HOA, ~1350-1450 potential rental price.

Some researching into that should tell you about what you can expect over the next 10 years.Every property should have at least these expenses listed out: Monthly Mortgage payment Taxes Sewer and Water Trash Heat/Utilities HOA/Legal Cap Ex and Ops Insurance Mgmt Fee Vacancy Once you have those accounted for, you can better understand your options with any property.

Additionally, dealing with an HOA can be difficult.

I'm unsure about the HOA fees, property taxes, insurance, and maintenance fees when it comes to percentages. 

You need to provide them with a specific statement that the unit isn't under rent control or no-fault eviction, that you have the right to kick them out if you plan to move in, info on bed bugs, mold, and lead paint, HOA rules, etc. 

However, today I get a call from the HOA saying that my unit is leaking to the unit downstairs.

Distressed seller is a Vet going through divorce who owes approx $31k on mortgage and approx $6k in HOA fees.

He has stopped maintaining the lawn and last month the HOA charged us a $300 fine for non-compliance for "failure to mow the weeds". 

I received a call from my lender explaining that because the Community HOA said that over 50% of the units are NOT Owner Occupied, we must put down 30% down and not 20%.