Our biggest hurdle is the financing aspect of it and we both know a couple of people locally who may be able to help, BUT we are wanting to start learning as much as possible to turning this idea into a future career as we both like the idea of employment independence as well as financial independence.

Our biggest hurdle is the financing aspect of it and we both know a couple of people locally who may be able to help, BUT we are wanting to start learning as much as possible to turning this idea into a future career as we both like the idea of employment independence as well as financial independence.

You may have the means or it may be unreasonable I have no idea but here's my suggestions.1) Look at a duplex or multifamily where you live in the one unit and rent the others out to reduce you living expenses2) purchase a single family home that you can convert a section of the home to a suite with a separate entrance, rent out the suit and house hack3) If you're on the road a lot, perhaps as a consolation would be to have short term rentals (STR) like an airbnb situation while you're off on the road.

However there could be a way for them to purchase a property using the 1031 exchange that they later convert to a primary residence in a few years when they fully retire.But there's a huge hurdle first and that is that the LLC is actually the tax payer for the property they are selling. 

I've been analyzing deals for a few weeks now and am getting more comfortable with the process, however, one of the biggest hurdles thus far for me has been trying to estimate what a rehab will cost on the varying properties I've looked at. 

Looks like the biggest hurdle, though is running a business in a residential zone.

Leaving your job will pose hurdles but nothing is impossible.

I moved your topic to the wholesaling forum since your question revolves around that topic as opposed to rehabbing.To answer your question, in today’s competitive market, finding buyers is not the problem, finding actual deals with enough meat on the bone is the hurdle.

Adding up taxes, debt service and any property management seems to make it an unreasonable investment at $300k.  

Unreasonable offers are unlikely to get a counter offer and in sellers will be turned off from trying to negotiate with you.2.