Converting primary residence to investment property

[Christopher McConnell]

I am interested in using my current primary residence as my first step into building a rental portfolio as it is on a good trajectory of increasing value and I have a desire to relocate to another area. I am considering renting out my primary residence and purchasing a new primary residence, but I am unsure of the best path to do so or what challenges I may encounter.  The details are as follows:

1. -Current residence purchased ~4 years ago for $300k with a conventional 30Y fixed
2. -I have ~$280k left on my mortgage, paying $1900 per month
3. -Current market value assessed at $440k
4. -I estimate I can rent the property for $2500 a month

Current plan:

1. -Complete refinance of current primary residence (Objective: obtain lower rate and monthly mortgage payment, remove PMI)
2. -Move into a rental property as a temporary residence
3. -Rent out my previous residence
4. -Purchase and move into a new home 
5. -Move rental property into an LLC with the intentions of continuing to add investment properties in the future

Areas of concern

1. -When I complete my refinance, what do I need to look for in my new mortgage to ensure I don't have any issue converting that property from a primary residence to an investment property and then deeding it to an LLC?
2. -When I apply for a mortgage on a new primary residence how will my rental property impact my approval? (I anticipate a net positive cash flow on the property but will likely not have more than a few months history of it)
3. -I plan to be able to cover the down payment and closing costs for my new primary residence with available cash, but am considering taking cash our during my refinance, or use a heloc after the the refi to leave my cash reserves available for other investments.