I can get coverage through Texas Windstorm Insurance Association (TWIA), but they would not insure without a new roof that meets their standards.

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Even if the PM did handle the eviction there would still be costs associated with it that the owner would have to pay. 

I've included an example below to help illustrate this.So different lenders have different rates (which do vary even for DSCR loans) but these are factors they all consider.See example below:DSCR < 1Principal + Interest = $1,700Taxes = $350, Insurance = $100, Association Dues = $50Total PITIA = $2200Rent = $2000DSCR = Rent/PITIA = 2000/2200 = 0.91Since the DSCR is 0.91, we know the expenses are greater than the income of the property.DSCR >1Principal + Interest = $1,500Taxes = $250, Insurance = $100, Association Dues = $25Total PITIA = $1875 Rent = $2300DSCR = Rent/PITIA = 2300/1875 = 1.23If a purchase, you also generally need reserves / savings to show you have 3-6 month payments of PITIA (principal / interest (mortgage payment), property taxes and insurance and HOA (if applicable).

He is the VP of the local REI Association and an all around great guy.

The entire town is in a property owner association(basically and HOA).

If this is the case Step 1 is to determine a fix and the associated cost.

There's a lot of lobbying by NAR and the other associations, too.Most consumers don't know how any of these things work and don't want to, and would sue anyone in a heartbeat if anything went wrong, so it's important to keep that in mind.There is always the path of becoming a wholesaler, if you really do know what you are doing.

Housing prices in Beloit are definitely cheaper than Janesville, and Janesville is (for obvious reasons) significantly cheaper to invest in than Madison.Can't be of help to the property management part though... we've looked and looked but haven't found a company we are comfortable with... your best bet there would be to join up with the Southern Wisconsin Landlords Association and network for a quick recommendation. 

I do not like this as obviously if a business account is only accumulating rent from 1 property, it wouldn't accrue the cash in each as quickly as it would if all of the rents were funneled into one account.. and it makes paying the bills a bit of a pain on each of the properties as I am having things done to the properties, lawn care, etc.. constantly has me making owner investment deposits into each to cover initial expenses associated with the properties.. etc.