@Samuel Metcalf- Most HELOC lenders  only lend on primary homes ...the  few lenders that do HELOCS on  rentals will likely have a low  CLTV   ( and a high margin over prime  which will lead to a rate in double digits ) .. check  with the banks / credit union located close to the property  and  also maybe there will be some feedback on this thread  pointing towards lendign sources that might work 

It's great to have you here.Here are some recommendations for you:Find and connect with other BP members that are in your area: http://www.biggerpockets.com/m...Set up keyword alerts to be notified of the topics that interest you: http://www.biggerpockets.com/a...Read Beginner’s Guide: http://www.biggerpockets.com/r...Check out BP Money Podcast: https://www.biggerpockets.com/..Wishing you the best!

San Diego has some spotty regs here and there plus it requires a permit of which there are waiting lists.https://www.sandiego.gov/treasurer/short-term-residential-oc...Check the address against the zoning and read those regs to make sure you can do it at that location.

Have you checked out the Real Estate Events and Meetups section?

I’d start by checking out the OTA’s and see what people are renting and in what areas.

@Jonathan E Francois Hopefully, you've already found different opportunities, but If you're still wondering, I would check out these guys: Multifamily strategy.

But they do not have the ROI that many expect, so check your numbers carefully....if you are doing this just for the $$ return you may be surprised.

there are a few heavy hitters in the MTR space that you should check out on IG and they all have educational offerings - jesse vasquez, amelia mcgee, grace gudenkauf, and sarah weaver. sarah weaver also wrote a book sold on BP called 30 day stay. that's a great place to start!

If you guy's are looking for a market that is set to see great appreciation, i'd check out Columbus, OH! 

You can do better than both of those options you just need to check out more programs for investors.