It was a block away from our favorite bakery and coffee shop.

As you've probably heard, Indy is a very "block by block" market. 

I live in Colorado, which is also the only place I've invested thus far, and am used to paying 1/12 the property tax I would pay in Texas, so it's proving to be a mental block, and I'm trying to learn more of how other investors negotiate high tax states.  

This is plenty to work with, but I think the only road block is having the equity available to sell your home if you use the HELOC, at least with the time line you explained. 

Would a beachfront condo be more marketable vs a townhouse a block off the beach?

No pain, no gain. 

@Rachel Gill listen to the newest podcast, she talks about her problems starting out every business has growing pains i do NOT listen to anyone that is not in this businessif you love this biz never give up,it will pay off

Something is blocking me.

Obviously someone can sue for anything and it is a pain even if you are right and win. 

Kyle Penland Pools up here are seen as a liability as much, or more, than they would be a sought after feature - the cost of winterizing and maintenance makes them a royal pain, especially since there are several very good public pools in the area.I would never have one at a rental ... nor in my own yard.