If you're buying a flip project, you'll either need a Vacant Dwelling policy or a Builder's Risk policy. 

As such, we have chosen the strategy of building an expanding portfolio of investment properties.We are interested in acquiring multi-family dwellings throughout the midwest, and maybe Atlanta (more on this in future posts).

Generally, rented dwellings cost more then owner occupied homes to insure if the coverage and limits are the same. 

(B) A cause of action may not arise against an owner of real estate in a covered transaction for failure to disclose:(1) that the subject real estate is or was occupied by an individual who was infected with a virus or other disease which has been determined by medical evidence to be highly unlikely to be transmitted through his occupancy of a dwelling place; or(2) that the death of an occupant of a property has occurred or the manner of the death; or(3) public information from the sex offender registry as defined in Article 7, Title 23.

Still have   5 mortgages, which includes our  own dwelling(non over 550 a month)...

Their original cost plus the value of any improvements made to the property over the years minus the original cost of the land the dwelling structure sits on will be their basis for depreciation. 

I want to make sure we're abiding by the rules and legalities in regards to the VA loan.Also, as an exit strategy, when we have to move after three years, my thought is that we should just rent out the home and the second dwelling so that we're getting more money than just breaking even.

**Disclaimer to point #1: If you are unable to find an Insurance Company who will cover your dwelling with a Pit Bull animal on-site, or if you are required to pay a substantially higher premium as a result of the Pit Bull animal - I think a very strong case could be made on your behalf that this is an un-reasonable accommodation that you would be required to make to rent to this tenant.

If the accessory dwelling unit (ADU) was constructed in a workmanlike manner you should get the necessary permits. 

If you are remodeling it first they will probably have to insure it in stages (Builders Risk & Liability policy, Vacant building, Homeowners/Dwelling Fire) .