Where do you decide to place one ?

So, for one time only, I will answer the questions and statements, one by one.1.

Test him and ask if he can give you 2-3 choices from his portfolio.If he gives you a line that this is his "best" one, or that the others are spoken for already - WALK AWAY!

The 2 best ones I know of are:- House Hacker Mafia (https://www.meetup.com/house-hacker-mafia-real-estate-invest...)- Colorado Springs REIA (https://www.meetup.com/colorado-springs-real-estate-investor...)Hope to see you at one of them!

There are no free lunches man.I'm not an attorney so everyone should confirm with one. 

Some other investors had purchased it to flip it and decided they had too many projects going to handle one this big.

Going to try out PayRange, the Shine Pay is slightly more expensive and the one quote about the 20 units appears to be from shinepay as it is the only qoute they ever made... not sure which is better but both look like good options

Find a new friend.I would get rid of them for just one of those issues.

Also, the tax benefits you expect might be over-hyped: https://www.biggerpockets.com/forums/51/topics/1075919-five-...Figuring our whether there is a useful tax strategy in your situation would take a one-on-one consultation with an experienced tax strategist, and here is how to find one: https://www.biggerpockets.com/forums/51/topics/1222774-expla... 

When we moved, we turned it into a rental, hoping this would be the start of our real estate journey—something we’d like to continue once my husband retires.Some key details:My husband is active duty and will retire in 3 years.We have one final move coming up this summer to Raleigh, NC.Our current debts are crippling us—the high interest makes it tough to stay afloat every month.The plan me and my husband are thinking bout:Sell the rental property.Use the proceeds to pay off all our debts, set aside emergency funds and a down payment for our next home.Free up $1,500/month from debt payments, and that also can stash in a high-yield savings account.Regain full VA loan entitlement, allowing us to purchase a multifamily home and use the house hacking strategy for up coming move.Avoid capital gains tax, since April marks five years of ownership, and the tenant’s lease ends in May.This wasn’t our original plan, and we hate the idea of using our equity to pay off debt.