Older brokerage houses are struggling to compete, and are somewhat in decline.

If something like the furnace or water heater goes out you will be struggling just to afford it.Always have an exit strategy in case things don't work out and trust me there will be times they don't.If you buy the property and after the first year both your roommates move out then what?  

In Massachusetts, it has always been a struggle to get the asking price. 

As mentioned by the others, management is always going to be a struggle for both you and your prospective property manager.  

I think even you would recognize though that not everyone was as prepared as you were and they struggled through those declining periods.

My initial struggle is figuring out financing.

Yes, So sec8 vouchers will PAY MORE.That is why i struggle to find a proper listing price.....So just list my properties at the SEC8 pricing guidelines?

Thus far we've targeted long term renters but if we continue to struggle with the back unit, we have considered short term, especially because we are in close proximity to the new arena. 4.

I struggled with it for many years until I tapped into what it took to actually develop confidence and extroversion. 

Houses are a lot cheaper, but I don’t know if I feel too comfortable living there for obvious reasons, and I’ve heard countless stories of people who struggle to get tenants there to pay rent.