I haven’t seen a property where trimming the bushes and fixing a fence will warrant a 25% increase in rent, much less a 40% increase.

I am a bit mixed on if we could benefit from a decline because we have the 2 Mission Beach STR units (a Single duplex) so it would suck for them to loose value, but we still have enough assets that we could potentially buy if the price warrants. 

That's a big steaming pile of nope, nope, nope.If this were a review on a public site, then certainly a reply is warranted.

The biggest negative is you have no control of HOA fees and if Condo is Non-Warrantable harder to get financing not to mention dealing with any HOA is always challenging.To answer your question yes you need a Property Manager that works for you not the HOA..

But if you do a search for "due on sale called" in the BP Forums, you'll see it happens often enough to warrant caution:But wait, there's more: The due on sale clause is not the only risk.

My advice is, read the fine print and understand the economic trade-offs you’d be making.You can come out ahead, but usually not as far ahead as appears on first glance, so make sure you understand the full deal that you’d be striking.The few that I investigated, I decided limited my future options too much so I chose to pay market interest rates to retain my flexibility with the property/project, or in other cases decided not to pursue the project at all regardless of financing terms.One important thing to look for is whether the financing (and obligations) transfer to any future owner and if so, under what terms, or if they do not, and instead trigger some kind of backout/payout clause on you.Many of those tax/loan programs stretch out over years, and since it’s hard to predict the future, it’s also hard to understate how they can limit your future options with the property.For example, many times we’ll do a 10-year holding projection initially but market conditions after only 4 or 5 years might warrant considering an earlier exit.

Likely not enough gain to warrant the cost/hoops of a 1031. 

If that warrants an umbrella policy, you should talk to a good insurance agent in your town to find options that benefit your specific situation.  

If so I can understand but just probing to see why this warrants full price.Any idea why the seller wants to sell?

Can't say I'm familiar with HVAC prices in Denver but I don't think the age of your current unit warrants that kind of investment.