I know I'd need permits to add an additional driveway over the drainage ditch between the road and I've already contacted contractors and the county for water and septic information so my main concern is the separation of the land I want to keep using from the tenants. 

This will provide him with a steady source of income as he's moving into his new home and provides you with additional flexibility.

If you looking to update the back for added square footage I would visit an architect to redo the plans or asked the city can they grandfathered the additional square footage.

They both have "regular" jobs in addition to this -- she sells houses, he fixes them.

I have received late charges in addition to monthly rental fees.

Additionally, there is no dryer vent so I will have to add one and it will have to vent up, which according to my handyman is not recommended.My question is -- does anyone have experience with ventless dryers?

Many great tenants would not even consider signing a 2-year lease, so you may be missing out of some of the market.From our rental criteria:FINANCIAL/CREDIT HISTORY1.No outstanding debt to previous rental property owners.2.No outstanding debt to utility companies.3.No outstanding debt in excess of $1000 that is not in a payment plan.4.No excessive monthly financial obligations - more than 20% of income.5.Lack of credit history or marginal credit history may result in additional security deposit. 6.Derogatory credit (past due accounts, collections, charge off accounts, tax liens, judgements in excess of $1000 and/or bankruptcy) may result in additional security deposit or denial.

Additionally, I learned that 90% of condo owners, in this building, actually are renting out their units.

Full search, perhaps additional risk premium.

I agreed to review existing report, in addition to getting my own inspection done by an inspector I trust.