I would recommend considering conventional financing until you reach Fannie Mae's limit of 10 properties, then consider either a portfolio loan, and start your race to 10 again, or look at DSCR at that time. 

Consider all the things that could go wrong and see if the lease addresses them: unauthorized pets or tenants, early termination, security deposit, lease violations, late rent, eviction, lawn maintenance, parking, etc.5.

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Both houses have detached garages and I have been considering turning the garages into 1 bedroom units. 

That's it, but a) print out a page for each property you think is comparable, b) make the list of repairs long and inclusive of everything you've done. c) Put larger items first like kitchen remodel......and don't just say 'kitchen remodel', list things like 'custom backsplash tile/Bosch appliances/recessed can lighting/pot filler/etc. d) Cite the price/value of the work done, and don't be afraid to be generous.

It’s a good idea to speak directly with an insurance agent who understands multi-unit properties to customize coverage for your specific situation.

Consider this, as an “experiment”, 24 months ago I invested $300,000 in equal amounts ($30,000 in each) in 10 speculative small REITs.  

I am considering Goodegg investment too.

I'm considering becoming a new investor in Middletown, NY.

Have you considered specific local market conditions?