And what type are looking to buy, SF, 2-4 MF, or 5+ MF? 

Hey @Mike Nelson, never assume anything about STR rules and regs.Here is the STR rules for Oak Park - https://codelibrary.amlegal.com/codes/oakparkil/latest/oakpa...I would call the city and make sure it is legal for a specific property.Now regarding the famous person angle, sure it can add value to the property or as a STR, but for STR use, I would think you would need it to be in original condition with a lot of the furniture and knick-knacks that were owned by the famous person along with a bunch of photos etc featuring the famous person.If you buy a place that has been totally redone but was owned by someone famous but has no features or things that were theirs, then I don't see it being a draw. 

Quote from @Brandon Vukelich:If you buy a vacation rental in Hawaii, then you're tied to that location.

Financing seems to be tricky with IRA hence feel that its best to buy with self funding fully.

Which area did you buy your first property in? 

Investment Info:Single-family residence buy & hold investment.

.: As a contractor and flipper, I dont buy materials from retailers or online.

(or if they're primary buyers, they don't care about yield, since they're going to live there.)i just went to visit two very distressed properties yesterday that i would buy.... if they were priced 50% lower.  

Focus on analyzing properties and starting small, like house hacking or buying a single-family home to rent out rooms, while ensuring cash flow and maintaining an emergency fund.

I would suggest you do both of what you suggest - meaning get either a new mortgage (more conservative route) or HELOC on the townhome and use those funds to buy your next investment property.