My idea is to run a website providing owners access to a reservation calendar so they can see what's going on, block off dates, etc. 

I am considering a deal in my market in which I found a significantly underpriced parcel of land blocks for major transportation hub in a gentrifying area. 

I would identify in the agreement profit splits, exit strategies, and management of the project to say the least.It depends on your strategy really...if you are doing fix and flips, then there are so many different opinions on little things like even what color to paint the walls, so as you can see, this form of investing has a lot more details that would need to be hashed out with partners.To keep it simple, I would suggest buy and hold, with profit splits, and predefined exit strategy, and maintenance. 

Several months ago I was looking into seller financing but as I did my research dodd frank was a road block.

generally it comes with a five to ten year color guarantee.

Also, about 7 to 9 homes have been sold within a 10 block radius with similar sqft and style for $300k+.

OK Everyone I'm in a little bit of a conundrum and I think personal feeling may be outweighing the business side so I need some help from a outside opinionI have 4 rental properties all showing a good return in less than ten years they will be payed off and showing much better,the wife and I are tinkering with the idea of moving out of state, and we have a great property manager available that would be extremely cost effective. we currently use him-on one property to " try him out "We currently have a FHA loan on a 30 year 27 left 3.5%currently payout 950a month that includes taxes and insurance and a pmi that will falloff in two years lowering the note but about 150.although once we don't live there we will loose homeowners exemption thous increasing the note by roughly what the pmi drops.insurance will however be lower because we would drop it to the commercial policy that we have the other rentals in instead of a personal dwelling policy.its in a b- area up the street from the high school and 1 block from the historic district.two bedroom duplex's next door get $750 a month.rent in that area isn't extremely high so I am figuring a rent of $1250 after property management fees thus netting a 300 return before any repairs. recently upgraded the inside so hopefully that wouldn't be a issue for a few years but you never know.my question is would it be worth keeping?

Nice attitude you have, glad people can see your true colors here. 

Wooden fences are rare; fences are normally concrete block so little maintenance is ever needed.

If the chimney is not essential (i.e. no boiler or furnace using it) block, disable (and down the road remove) it - chimneys, particularly those with traditional fire places, are major sources of heat loss.