From a legal perspective, I would suggest having separate LLCs for each business venture.

Sometimes the solution is to team up with an investor in what is called a Joint Venture.

Some call it partnering but the better solution is Joint Venturing.

All that said...if you're not confident you can get at least 1.5x your LT rents as an MTR, I think I might go with long term but skip the management company and DIY. 

This is not DIY stuff, it requires professional help. 

With a strong passion for hospitality and a commitment to exceptional guest experiences, I've launched this venture to offer premium accommodations that cater to the diverse needs of travelers.

And just rode the wave of RE through all sorts of different RE ventures..

As for when to call in a contractor, it really depends on the scope of work and your comfort level with DIY projects.

If you're successful, you can use earnings to fund your own ventures.

My strategy would be to protect the money optimally from the government and from other potential filters and to optimize my time to do what I enjoy doing instead of worrying about real estate ventures.