But that is like in any international destination at the moment because of Covid and the Riviera Maya (including Cancun) is probably one of the least affected areas as it is one of those that accept visitors and on of the very few that accepts American visitors.

., more than half of the calendar year) for the Borrower's personal use and enjoyment·The Borrower may rent the property on a short-term basis provided that the property is not subject to any rental pools or agreements that require the Borrower to rent the property, give a management company or entity control over the occupancy of the property, or involve revenue sharing between any owners and the developer or another party·The Mortgaged Premises must be in such a location to function reasonably as a second home·The second home must be suitable for year-round occupancy with the following exception: a second home with seasonal limitations on year-round occupancy (e.g., lack of winter accessibility) is eligible provided the appraiser includes at least one comparable sale with similar seasonal limitations to demonstrate the marketability of the subject property.

Many of the potential deals we run across are not suitable for conventional mortgages, you would need to pay cash or use a lender who can close quickly (hard money lender).

Then you should think of places you want to visit or live, or are very familiar with. 

Plus if you need repeat the process down the line you will have a suitable template.Using a generic one from the Internet increases your risk when / if things go wrong.

Unfortunately the cost to build in my area has risen in the last 20 or so years so that a new build isn't very suitable for a house hack situation without having to cover a large chunk of the mortgage yourself.

If I could not find a suitable assignee, I would have closed all cash for this property and used the delayed financing exemption.

Be sure that you have a clause that clearly indicates that visitors can stay for X number of days and that any stay longer than that requires LL approval.

I am somewhat familiar with Baltimore and the different areas, but if I find a half decent neighborhood suitable for tenants, What is the market like?

Maybe there were, it's not really my area.I remember one court case where symphony musicians were not allowed to deduct the cost of their performance tuxedos, under the theory that those clothes were suitable for non-business wear.