Need some opinions on which path forward

[Bernard Walter]

Hello,

My name is Bernard and I want to move more into real estate. I currently own a townhouse(primary) and a property with two 1920s beach cottages that are currently rented. I have owned the rentals for 2 years. Currently I’m at 6.75% and it cash flows about $100 a month. Till insurance sky rocketed this year. Did some wind mitigation so insurance will come down some. Will still need to raise rent to cash flow. 

I looked into getting a cash out refi. Right now the Mortage is $3668 and should go down to about $3,480. The refi would raise the Mortage to $4,400 but I will get $103,000 after everything. 

The back house is rented at $1750 and the front at $1600. The front house is rented to my friend who also kinda acts like a property manager. Don’t really want to raise his rent $500. The back house lease is up in June. I’m pretty confident I can raise that rent to $2200 but the tenant is a great tenant and pays right on time. If he decides to leave I am not worried about renting it to some one else. 

I don’t want to take a chance ruining a relationship with my friend so if I did a cashout refi. I would be paying $500 a month myself.

My primary residence is at 4.25% and I can also get $100,000 equity from a cash out. It would raise my Mortage about $500 an month. I was thinking of refi on both properties and purchasing a couple duplex or multi family. Don’t necessarily want to refi my primary because I only owe about $100,000 on it. 

Please can some one help with some guidance?