The investor is obviously doing a lot of things incorrectly (and you shouldn't want to work with him), but you're also doing a lot of shady things:- No insurance- Not pulling permits- Not filling out a W9 (or charging for taxes separately)I would suggest you cut loose from this investor, but that you also examine your own business practices and make the appropriate changes there as well...

However here me out: I have completed law school (in Australia) and had some experience writing and examining deeds before.

Buyer has examined the Premises and is relying solely upon such examination with respect to the condition, character and size of the land, improvements and fixtures, if any, constituting the Premises.At Buyer's own cost and expense, Buyer shall obtain and maintain in full force and effect at all times during the continuance of this Contract: (a) comprehensive liability insurance for bodily injury or death to any person or persons, and property damage insurance, in such amounts as Seller reasonably deems necessary; and (b) fire and extended coverage insurance in an amount sufficient to prevent Seller from being a co-insured under said policy of insurance, but in no event less than the unpaid balance due under this Contract.Seller and Buyer shall both be named as insured parties in the insurance policies required above, as their interests appear, Buyer shall furnish Seller with memorandum copies of such insurance policies upon Seller's execution of this Contract.

I passed my CT real estate licensing exam in January and I am looking for a Broker to work with in the Hartford area.

It is not possible to give an exact estimate from such a cursory examination but it does give a fairly accurate range.  

I don't want to speak to which strategy you should use for decreasing your costs, but I would recommend examining your tenant screening process if you are having to actually go through the whole eviction process that many times.  

He works with the loan officer who would assign the mortgage to an approved attorney (usually a friend) or he could tell them I am his attorney and it would come to me if I can be approved (write for a national title company, have malpractice etc) I order a title exam from third party title examiner.

Ive lost millions not examining this quiestion?

I plan mailing a yellow letter and have been examining my list by calling owners and asking if they are interested in selling.

Look at the bigger picture before the details, and examine possibilities / potential upsides, then the fast due diligence (what could go wrong, what am I missing that can bite me later).I'm familiar with the neighborhood.