@Anthony De La Rosa  I have been involved with a good number of clients looking to house hack here in Connecticut and here is how I would counsel you based on the info you provided.Do you really want to live in a low income area?  

But, I would consult an attorney in the matter since I am not familiar with Delaware.

@Bradley De comarmond I'll look out for the next one for sure - tonight's a little tight for me.

Do the calendars talk to one another at all or do you have to manually de-conflict them?

Say you were able to buy a cul-de-sac's worth of these areas for under 100k and turn it around after demo and resell to the town to build a rec park, or combine them and sell the land to build a strip mall, condo complex, etc.

In Delaware County they indicate they will pursue comtempt of court charges if you win the bid and don't follow thru.

Also debating if I really want my starter home to be a "revolving door" for my cul-de-sac?

They were bigger fish in residential pond but now a minnow in commercial.With a 1031 exchange you could exchange to own directly,look at a TIC (tenants in common) model, or a DST ( Delaware Statutory Trust).

If you put a property under contract for X, and assign it to someone for Y,  to make the arbitrage of Z,....that to me appears to be a de facto net listing, which is illegal in most states.

Joshua, I will do more research on the Delaware Statutory Trust (is that the DSTs you were referring to?)