You'll want to read Maryland new requirements for landlords.https://dhcd.maryland.gov/TurningTheKey/Documents/HB693-Land...

A land loan for 'raw' land will require a 50% down payment and high APR as you know.

Now, some states require an attorney to review contracts. 

In our experience, Remote Investing requires finding a PMC that takes the time to understand an owner's expectations and discusses if & how they can be met.A common problem is a percentage of Remote Investors expecting their PMC to be a personal assistant.

You'll need to meet requirements like parking and setbacks and might encounter additional hurdles in environmentally sensitive or historic areas.

Since your lender requires prior experience building and selling/refinancing a single-family residence (SFR) on your own property, you may need to adjust your approach.

And I will state different jurisdictions have different rules, processes, expectations, etc.In my area you are required to have a permit to swap a water heater.

If you have equity and decent credit, a conventional Fannie Mae HomeStyle (or the Freddie Mac version) would likely be the better option instead of an FHA 203k loan (which will require a 3rd party HUD consultant to oversee the deal in addition to having the contractor involved). 

There are certain things that require experience that DIYers just can't get right or spend way too much time trying to do.

In the last 18 months various states have instituted new rules, regulations or laws related to (1) need for licensure to wholesale (2) restrictions on marketing of a property in which you do not have ownership and (3) disclosure requirements when dealing with a homeowner that makes it clear to the homeowner that the contact signed with the wholesaler is not a definitive “sales” contract, therefore making it less likely home owners will sign4.