Hi BiggerPockets Community!

I’ve been reading these forums for awhile and have learned a ton of amazing information from you all -

I'm in somewhat of a unique situation (or perhaps not unique at all) in that I currently own one investment property out of state (downtown Chicago), but my renting it out was the result of an unanticipated move across the country and not of investment property deal assessment or financing. That said, it is generating positive monthly cashflow and has "forced" me to get my feet wet / served as a personal proof of concept for out of state investment.

I'm currently renting in a high-cost area of Sarasota, FL but am using my lease term as an opportunity to learn as much as I can about real estate investing to make as informed of a decision as possible about my next purchase. Currently, the concepts I'm looking for guidance / perspective on are:

- Does it even make sense to plan to purchase my primary residence after this lease is up or keep renting and use my capital for another out of state investment property?

I live in a luxury apartment complex with all the amenities (which I use) in a phenomenal location (minutes’ walk / bike ride to the bustling downtown, waterfront parks, and beaches which has allowed me to comfortably live without a car and enjoy the things this area is known for). I also have none of the typical qualitative factors people take into consideration when purchasing a primary residence (i.e., family preferences, proximity to school / work, etc.). In my amateur initial assessment, the mortgage on a comparable condo / house that would maintain my lifestyle would be double my current rent with bleak cashflow opportunity if I were to eventually move out.

- Out of State Investing in General

In today’s world, we have all of the online tools to make this a successful, repeatable strategy (it would appear). However, I know there have to be many pitfalls with this (lack of familiarity with neighborhoods makes deals make sense on paper but are a disaster waiting to happen in reality being one that comes to mind).

- Partnership

This seems like a very attractive route for my current situation, but I am unfamiliar with the tactical first steps and what apparent value I would provide to a prospective partner in out of state investing.

- Feasibility of BRRRR

This is a strategy I've never really considered as an option for me simply due to my total inexperience with doing any sort of rehabbing, sourcing materials, dealing with contractors, etc. This inexperience seems twice as daunting when thinking of it in the context of an out of state property. Before I completely exclude this strategy, I'm curious if this rationale is sound of if it is simply making excuses.

I know this was a ton of information, but I'm definitely excited to continue learning as much as possible and begin networking through the wealth of knowledge / individuals on this site. I know how easy it is to get into analysis paralysis with REI so I look forward to developing my strategy over the coming months so I can put it into action in the next year.

Thank you all!

Andrew