Thanks It's a derisive term for an area where the government and community make excuses for bad behavior by calling it a "disability" and enable that bad behavior by protecting said person from "discrimination" based on their bad behavior, usually at the expense of hard-working people.Merely explaining the term, no judgements made. ;)

This will save us so much money and enable us to go take down another hundred units.I was wondering about the rules and regulations or pros and cons of 1099 vs.

It won't take long for the current tenants to learn your management style is different from the previous owners if you spend some time up front at the property and your presence (or that of your designee) is visible.It may be that some of the current tenants are enabling homeless people.

Partnering with other people in the same situation as you may enable you to take down a larger asset together. 

If your'e capped due to your entitlement being tied up in two homes, refi the investment property into a conventional loan (yes, your rate may be a little higher as an investment), but this would enable you to do a one-time restoration to restore your VA entitlement to the full benefit, and then do a VA cash-out refi up to 100% on your primary to pull out equity for down payment on a new house.

Then, partner with her on a couple of more deals where she could utilize her cash via a 1031 exchange, enabling pocket money and no capital gains. 

The big downside I see with this approach is that we could only purchase 10 properties with loans through Fannie Mae/Freddie Mac if both our names are on each loan vs. being able to purchase 20 properties through Fannie/Freddie if we purchase each property in only one of our names.2) We both have solid W2 jobs and essentially no debt outside of our investment properties, so once her credit score is about on par with mine, would our improved DTI when applying for loans together enable us to get better lending terms to the degree that it still might be worthwhile to purchase 10 properties together instead of 20 properties individually?

Be professional, take good care of them, fix things when it needs it, have grace when it makes sense (grace DOES NOT mean enable) but run it like a business. 

My tax situation is slightly complicated-I'm a RE investor but also a self-employed musician and handyman so there's lots of business-related deductions; nothing too crazy but enough that I don't want to do it myself.

A 30 year fixed mortgage would have enabled many landlords to hold on to properties they lost in the 2008 implosion so it is a big deal.2.