I also don't think landlord insurance would work since it would still be my primary residence.

Additionally, the correct kind of insurance for our set up here is over 2200 a year (will be cheaper if this was not also our primary residence) and we work from home and desperately need better office space.

We are taking it slow but currently have a trip planned to sit-down with the agent we have lined up and he has agree to take me around and show me what fits into my plan I have outlined to him in a previous phone conversation.My feelings are that you can easily expand into this area but my only recommendation based upon your primary jobs is to take it slow.  

Including my primary residence I now hold 5 mortgages.

I have a primary property and a rent house.

This would be my first and only mortgage, so he said I could claim it as a primary residence and still rent it out.

For that matter, neither does the balance of the underlying primary loan.In general, you’re assessed capital gains taxes on the difference between what you pay for an asset (your basis) and what you sell it for.

But primary residences have exclusion ($250k single and $500k for married).

I have purchased three homes with the same $30k from a HELOC on my primary home.

How would I qualify for a conventional mortgage if there are multiple units (fewer than 4) for either a primary or second home?