Not only do I not want to deal with the restrictions on a regular 203k loan but I also wouldn’t qualify based on current credit score still damaged from being young & reckless. (510 FICO) total debt is only around 6k (I know, I know, I need to take care of it).

Get a regular marketing campaign going so that you have deal flow first.

Check buildability/restrictions with the local building dept.In addition on this vacant lot....check the zoning and land use classification, wetland classifications, etc. none of which will be part of a title search/insurance.People typically wanting to “avoid red tape” are looking to dump some problem onto an unsuspecting sucker.

whereas those in the wholesaling game are constantly spending money to create income.. it never stops. your only as good as your marketing campaign and your ability to close. 

I am starting out on my first marketing campaign.

Hopefull your father is not that old to encounter this issue(There is a time restriction of 1 year).   

My list of properties is increasing and I am looking to start a direct mail marketing campaign to get in touch the owners of the duplexes.

Possible, with a blanket loan covering both properties, but not advisable....it restricts your ability to sell, refinance, etc. individually.  

Condos are also complicated because you then need to find out if there are rental restrictions in place because they could prevent you from renting at all or other restrictions.

I'm about to embark on a lead gen campaign (direct mail + social media and Google ads).