If I decide later to start a construction business (actively building and selling new spec houses), assuming this is taxed as ordinary income with social security, etc and treating the homes as inventory - if you build a house, then sell it, then spend that money building a second one, but don't sell it until the next year, then sell it, then build another, can you effectively push off the taxes as you are rolling the sale proceeds into new inventory costs / construction costs? 

Security deposit can be used for damages on the property that are not ordinary.

Still learning and working out a way to attain financing since my employment situation is a little out of the ordinary, but otherwise have a bit of cash to put into a few investments.I've also been working on a spreadsheet the past few months, though I'm always tweaking it.

Regular landscaping/yard care (mowing, edging, trimming, fertilizer, weed control) will be provided by ____(check one)____ [   ] Landlord  [   ]  Tenant .For all Tenants:a.Tenant agrees to keep yards, walkways, patios and decks clear and to keep premises free of junk and debris.b.Tenant accepts liability for all landscape damage and/or replacement of such, if caused by neglect, abuse or lack of water.c.Tenant may plant the beds adjacent to their dwelling to their liking, but only with those plants that are of appropriate size and type for the beds.All plants brought or caused to be brought to the property by Tenant will be cared for by Tenant.d.Tenant agrees not to cut or prune trees, hedges and shrubs.This will be Landlord’s responsibility.e.Tenant agrees to properly dispose of all plant debris and agrees to not leave such on the property.f.Landlord will consider special Tenant requests for planting and removal of plants, shrubbery and trees, but reserves the right to determine the make-up of the landscaping.g.Tenant agrees not to grow marijuana on the premises, indoors or outdoors.For Tenants of single family homes only: a.Tenant agrees to mow, water, and keep the grass, lawn, flowers and shrubbery thereon in good order and condition, applying fertilizers and weed retardant as needed. b.If Tenant fails to keep the landscaping in good order and to follow these guidelines, Landlord reserves the right to hire a landscaping service at Tenant’s expense (after a 10-day notice to perform covenant).c.Landlord reserves the right to restore the landscaping to its initial condition, as it was at the time Tenant began occupancy, or if improved during Tenant’s occupancy, to the level of such improvement.

Original single story home, built 1953, has been totally remodeled with 3 bedrooms, 2 bathrooms, wood burning fireplace, covered rear patios & more.

It can handle any storm when it's clear but if any debri blocks the drain, it can fill up the patio area and flood the basement.

Is it out of the ordinary to ask to do a walk through with a contractor so that I can bring some concrete numbers to my buyers?

Not sure if a bankruptcy would change the parameters or not but that may be a better option for the seller. yes if the bank reports the debt as forgiven.. there is an IRS form though you can file with your tax's that says your broke.. then you don't own the tax's on the forgiven amount.. during the crisis IRS postponed this so no one got that treatment but that sunset and now short sales or debt forgiveness needs to be calculated …. the forgiven debt is tax as ordinary income so a 1 mil forgiveness could be a 300 to 400k tax bill..

Additionally, I'm not certain but I believe that every penny of withdrawal taken out of a (non-Roth) 401k/IRA during retirement is taxed at your ordinary rate, which is likely to be higher than tax preferred treatment of real estate.

As far as an s-corp, it is not usually a good idea to hold rentals in one, as there are issues if your strategy changes in the future.S-Corps may be beneficial if the income you are producing from real estate is ordinary income and subjected to self employment taxes (like flipping homes, wholesaling, property management).Be sure to talk with a CPA that knows your entire situation before making this decision.