Also, the drawback of the HELOC is that it is a variable rate so if rates go up, which is very likely, your payment will increase and you need to account for that in your investment evaluation.

What are the drawbacks of cash flowing $1k/mo. even if you still owe on them?

I haven't shared that thought with my lender yet though.My lender wants to sit down and discuss the benefits and drawbacks of going FHA versus Conventional.  

The draw backs of listing a property with a tenant, with a valid lease in place, is tenancy/occupancy rights (different in each state) it can make marketing the property difficult; you would most likely be bound to market to investors and we all know that end users will pay more for a property they love.Naturally, a seasoned investor would say, just sit tight and wait for the turn around; but, when your done your done, I totally get that.

There are drawbacks to every geographic area, investment strategy, etc. 

As someone who has done both I would recommend investing in Connecticut rather than at a distance.Like you mentioned, CT has its drawbacks and challenges, but the challenges will be there as well in another city/area you don't know that well while others manage your investment   

Payments must be made directly from the IRA and you absolutely should not pay any expenses of the IRA's investment personally.This is one of the little details that is a drawback of trying to use a custodian managed IRA for a complex asset such as real estate.A self directed IRA LLC or Solo 401(k) trust solves this problem by creating an entity you can control, which can be listed on utilities, insurance, etc. and for which you will hold the checkbook.

The drawback is you might lose your buyer. 

The drawback in outer areas would be less potential for higher than normal appreciation.

The benefit of bringing on my brother as a partner is that he knows the area well - which neighborhoods are better than others, which property management companies are good, which are bad, etc.Yes, there are definitely some draw-backs to renting to college students, but the vacancies and move-out / rehab costs are the main reasons I'm planning on hiring a professional PM to deal with all that.