Shouldn't be the goal.

My goal is to stack rentals with the profits from flips. 

Or, would my money be better spent someplace down south or by a National Park that would have year round traffic.My goal is to have a place where my family can spend a couple of weeks during the Summer, pad my retirement a bit, and have a place to leave my kids.Thank you in advance for your input.

Then talk to an agent about your goals and they will help you navigate what you can afford based on your pre approval.

I think of it as a range of rental prices of comparable properties and my goal is to make a good return on the lower end of that range of values.

She'll be presenting a variety of topics and open discussion, with the goal being "Make your STR stand out in a competitive market".What additional topics or specific questions should we be sure to answer that you wish you knew when you started buying STR's? 

House hacking is the most powerful way to get started in real estate investing, and it sets you up for success because you learn so many things: dealing with contractors, how to screen tenants, lease negotiation, but most importantly, your goal should be to reduce or eliminate your housing cost, and there are a lot of ways to do with house hacking depending on your flexibility with strategy: rent by room, Section 8, mid-term rental, STR, etc, and you can combine multiple strategies too. 

But we won’t qualify for a primary residence refi anymore, and I’ll need more equity to refinance as an investment property.Future investment goals: I want to own rental properties in the future, but I’m not sure if holding on to this one (which we already have) is the right move, or if it makes more sense to sell and build up savings for a better investment down the line.I’d really appreciate any advice on what I might be overlooking here.

But whether renting or selling is appropriate I think depends a lot on your overall financial situation and your goals.

(Luxury, first time home buyers, investors, etc)There are several others that may be specific to yourself but only you can decide your final goal.