Fishtown and Point Breeze are strong options but can be pricey.

(This option would would not carry any debt, all debt would be paid in cash)Or keep our current house, rent it out, and cash flow NET monthly about $1,500?

The cash flow is a bit sub par on this one and I anticipate some larger expenditures coming my way in a year or two so I'm contemplating this as an option.

If you do go the seller finance route, consider asking for a right of first refusal option in the event the seller ever decides to sell the note. 

The second son is married but has not lived in the home at any point during the last 20 years so this doesn't seem to present any options for savings.I thank everyone in advance for your thoughts. 

Curious if there are software options for managing both types of rentals.

The land banker, the long term landlord, the neighbor that wants to expand their home, or the horse owning owner occupant with no other options?  

The Purchase and Sale Agreement is the contract that you and the seller sign which allows you the option to purchase the property at the agreed upon price.

I met with Wicked Smart today and was told they help you set up a lead sourcing system, help you structure creative financing - which is essentially lease option/purchase, subject to and owner financing....all strategies I am interested in learning more about.

Seller will be taking a 30k+ loss with this route.325k with 50K down to seller, 3 years of payments $1600/month, and a balloon payment of 215k at the end of 3 years.Benefits to me: (1) 10k less downpayment, (2) with the conventional route, the loan would be at 228k after 3 years of payments, so I will gain additional equity with the 2nd option since I will owe 215k (presumably I will have to refinance at that time).Benefit to seller: she gets over asking price, 50K upfront and $300/month of cash flow.Does this offer and structure sound reasonable?