Need help understanding basic strategy

[Maxwell Lee]

Hi everyone, thanks in advance for your time and advice!

I will try to keep this first post short(er) and simple but may leave out important details as a result. Happy to expound more if necessary. We are somewhat ignorant about financing options and best practices. 

My wife and I have a handful of rental properties owned free and clear. Between the two of us we have our names on 3 mortgages, although only one has really come into play when we've discussed with lenders...the other two had no effect on us. We also have a HELOC with zero balance...we generally only dip into it when we start doing too many flips at once.

We are now planning to cash out refi on our rentals owned by us...working out options with a few portfolio lenders. However, our rentals have built up appreciation to the point where the CAP rate isn't so strong. Generally speaking we're looking at 100-125k ARV and rents at 800-1000/month. These are also in popular neighborhoods with desirable tenants and no trouble renting out at all. Also, I feel like we're approaching the higher end of our market now. It's not crazy high, but I would normally begin considering when in the next year or two is the best time to sell.

So my first question is...if we cash out refi is that almost as good as a sale if we decide to hold long term? We'd lock in our appreciation gain and the only real risk is if markets tank and our suddenly in-demand rentals can't rent for anywhere near current rents. Or does it make sense to cash out at a lower LTV...say 40-50% so that we're hedged a bit with stronger cash-flow. Or should we cash out just a few and sell the others? What makes the most sense from your experiences? I keep going back and forth lol.

My second question has to do with the larger financing picture. I have also spoken with a few lenders both conventional and private, on doing specific projects. I'm wondering what order is best for our borrowing power...should we be trying to do the smaller loans first to have a better shot at the larger loans? What's the best growth strategy?

Thanks again for your help!