$300-$400k will likely not get you even a 2-family in the best area of New Haven unless it needs a lot of work, but will get you a property in a top flight area of Hartford.

Do you include specific clauses in each of your subject to deals spelling out exactly how insurance on the property will be handled?

Similarly, if you put several Class D tenants in a Class A 4-plex, what do you think will happen to the property?

Knowing the rent will likely show up each month—even if the tenant has challenges—removes a lot of the uncertainty that can come with rentals.The people listing this apartment as a “Section 8 property” are likely trying to target buyers who value that stability.

I will pay the money if I can do 1 or 2 deals in the next 4 months.

This will simply causes prices to be even higher, and continue to constrict demand... 

As long  the tenants pay the rent each month, increasing their rent will be very tough and getting them to leave will be extremely tough. 

Same principles apply - being busy will create opportunity. 

I was studying the market and my rent will be just enough to cover the mortgage and HOA fee now I might to pay out of pocket for insurance but don't want to sell it yet because the area is growing and might have good appreciation in the years that follow.

Usually unless you’re willing to spend a bunch of money on marketing it will take a while to organically grow your network. 2.