I always thought it should have been outlawed and have no idea if it still exists in consumer loans.

Start-up costs are also deductible but are amortized over 15 years with a limit of 5k.Start-up costs have strict rules and your case might not be the same as this one.Case Summary:Timeline line of eventsStarted investigating property: FebPut first contract (canceled): MayBought first property: December 30thWhether a taxpayer is engaged in a trade or business is determined using a facts and circumstances test under which courts have focused on the following three factors that indicate the existence of a trade or business:Whether the taxpayer undertook the activity intending to earn a profit;Whether the taxpayer is regularly and actively involved in the activity; andWhether the taxpayer's activity has actually commenced.On the basis investor testimony, we may assume that he undertook this activity to make a profit and that he regularly and actively engaged in it.

My sister was suggesting I pay to clear off the existing run-down trailers and get my investment back in land equity.

If you hold it as a rental for 3+ years, you have created a tax liability that did not exist before.

They would grandfather in any existing homes that are licensed.  

Apparently it doesn't matter as they won't take any new ones, only renewal of existing.

Unlike STRs, a platform that analyzes vacancy, pricing, etc. does not exist. 

From my experience buyers typically prefer these lots because they will not have any neighbors directly behind them.I can't tell from your question if there is an existing house built, that you are purchasing, or if you are buying a lot and going to build on it.Also, you should have access to an interactive flood plain viewer to look where the 100, 500 and zone X for the flood plain are situated.

When you purchase a home "subject to" the existing financing, that is when a mortgage stays in the sellers name.

You are pulling strong equity out of an existing property to invest very far away, for the first time, and with limited to no contacts in the area.