I would suggest looking into a roth IRA rollover, however that in of itself is a taxable event depending on your mix of pre tax and post tax dollars going over to the roth IRA.

No reason to pay ANY pre-pay penalty even on a DSCR loan. 

The Riverside market (St Vincent's) and San Marco (Baptist main campus, Anderson Cancer Center and Wolfson's children's hospital) plus right next to downtown cover a good portion of the bases.

We do have the time to manage/clean and the capital to cover expenses while we learn and refine our strategy.We are currently under contract and plan to close April 1st.I realize that we don’t know what we don’t know so I would appreciate any feedback.Thank you so much in advance!

If you are saying they are too close to a hard money lender in terms of pricing I beleive what you are saying is they are the cheapest hard money debt you have been able to find :)  Ironically Spring Garden Lending came into existence when Univest acquired VG Bank many years ago.

DSCR terms are simply worse then a conventional loan meaning you will have higher closing costs and likely a pre-payment penalty (which can be even more expensive in the long run then the upfront closing costs).

@Tammy Muller here are two great threads that cover the accounting software options and feedback thoroughly: BP -> Quickbooks or something elseBP -> Fav bookkeeping/accounting softwareThey don't mention either of these options, but that might be because RentalHero &  REI Hub are full-blown property management software, and Quickbooks Online, Digb, and Stessa are accounting/tax software focused on real estate investors.

You are competing not only with HH'ers but investors as well.Now this is for Denver so may not be the same for Chicago.Here is what I would do:1. connect with agent that is familiar with HH'ing and has a solid track record. 2. connect with a lender to see how much you can get pre-approved for.

Insurance would cover it, I would pay the deductible, and no assets would be lost.If you are in an area like San Diego where people are more likely to sue, a judge is more likely to find you guilty, and the payout is likely to be higher, then you may consider an umbrella insurance policy.

The pull back in these markets is due to a confluence of many factors, but it started with these environmental factors:Low interest rates and easy financing for new projects.Structurally high rent growth on existing inventory.High wage growth and high job growth.Very low vacancy.These factors led to floods of institutional capital coming to these markets to snap up existing multifamily inventory and build new supply to meet demand.For these markets, the last 5 years have been a seemingly never ending party!