Wife also has a healthy 10% profit sharing. 

Your investment strategy should align with your lifestyle and investing goals.

These investing strategies I think also fit better with my current lifestyle (managing a full-time job. not for long I hope) and assisting my fiance with getting her business off the ground with any time I can spare.Thank you again for your post. 

Hello @Al CaanThe great news is that demand for STR is very healthy, especially within 15 miles of Disney, for obvious reasons. 

Safest path is to build up side hussle until it can support 1) eating and 2) tax returns that are healthy enough to get financing. 

In a competitive market such as this, having that return with limited down payment is actually a strong return and while you're not swimming in cash flow, you definitely are well positioned for your lifestyle and growth for the future.

I'm one of those people that never made money before, and fell victim to lifestyle creep with the more money I made.

Can you provide a healthy balance sheet that will help secure financing?

I also prefer people who have a preference for being a renter as a lifestyle choice.

I also really like my house, and moving into virtually anything multi-family is going to be a downgrade, so I have to decide if I want to accept that lifestyle impact.My conclusion so far is that a house-hack might not be a good idea; with the difficulty in finding enough space and proper layout for work, with the disturbance to my son's life (may not be an issue, kids can be resilient, but something to think about), and with the expense of moving each time.