This thorough process ensures higher chances of getting the desired price and timing.

Meaning is the area more desirable to buyers than to renters.

Are there any strategies for making this more desirable for the current lender? 

If you’re buying in a desirable neighborhood and have the capital to do fantastic design and furnishing, you will still do very well.

Find a GP doing deals in your desired market and partner with them.

I wanted to start by house hacking but (1) I am not allowed due to strict HOA rules and (2) my city isn't as desired as the next city over. 

I manage on Oahu in Hawaii and I would assume based on things that I have heard from other hosts and managers in CA that the conversation around regulation would be somewhat similar given that it is a highly desirable destination for both guests and investors in the STR space.Speaking only to what I have experience with here - there seem to be three types of zones that vacation rentals fall into - on one hand you have zones where they are illegal, and while it is possible to run and gun in these areas I don't think the risk is worth the reward if you get caught.

Land Acquisition: Look for land in desirable locations with good growth potential.

They acquire things but don't put very much desire into keeping them when they move.

That resume will determine your future.Prime example, buy a few lower than desired cash flow properties now and into the next few years vs. investing in a good yielding stock/fund at 7-10%.