Balancing job and investing stress requires prioritizing properties and strategies that align with risk tolerance and time commitment.

Premium increases are rippling through the market; the state is also always going to be financially strapped/high tax due to union pension commitments from past generations and the high tax, high services nature of Chicago.I'd highly recommend getting on a plane and driving around before you buy anything there. 

The key to navigating this market successfully is to stay vigilant and committed to this niche for the long term.

I just don;t see the demand.

Additionally, make a commitment today to at least spend a few hours a day learning about real estate investing.

Depending on your loan structure I'm not even sure you could legally offer a personal guarantee outside of the loan for that money without committing mortgage fraud, as anything that could hinder the ability of the primary lender to recover their principal is supposed to be declared during their diligence period, and any material changes up to the point of taking the loan are supposed to be disclosed as well.

I enjoyed the hard labor and comradery that I missed from my Navy days working in engineering.My question is, how do I go about getting more experience on paper without having to commit to an employer/contractor for a long-term position? 

Just because the information is not as readily available online doesn't mean there aren´t people (agents, builders, notaries, accountants etc)  and resources that can prove to be invaluable. 

The time commitment the HH properties took from our company made them simply untenable to continue to manage. 

Mortgage Rates are dictated by the bond market more or less, fed funds are typically a trailing indicator of the T Bills.No, your rates not going down.