It's easy to go after the shinny object, but putting in the long-term work on myself has 100% paid off.We are a Chicago-based GC-tech (general contracting technology) company but expanding into the Richmond market where my partner is.

You might change your investment objectives.

This will reveal maybe some potential objections.

Decide what level of spend you're able to maintain over the long term and then commit to it.Know your objective and design your communications to achieve it. 

There are many factors subjectively and objectively to consider.

David Greene always tells us that purchasing a property in Cali should be the first objective (ideally a househack), only go out of state if you exhausted being able to purchase a house in California first.  

Just plug in everything you can find and see what's what.Like @John Underwood, you need to use an objective eye on the place and make sure it makes sense as a STR.

I would not waste my money on a primary.Choice 1 seem to be unpopular but I'd like to be objective and ask in what scenario would this choice be appropriate? 

The number one objection a hard money lender is going to have with your stated problem is that your business plan got into trouble. 

Set your sight on a BIG target to reach a big objective.