.- Kids Toys:  We advertise to families and have another 2xKallax cubes full of toys that won't break and are tolerant of missing pieces, but are easy enough to cleanup:  lincoln logs, blocks, hard animals, stuff like that.   

Currently I think 200k being the upper limit of investment makes the most sense and is within my risk tolerance range.

@Keith RichardsonIt depends on your risk tolerance and ability to stay organized.

There's no one right answer for everyone since we all have different financial situations and risk tolerances.  

What is your risk tolerance, and are you ok with properties that need work, or do you want turn key?

I would focus on one of two things… finding a more tolerable high-pay work situation OR developing some coping skills to deal with your current working situation.

If you can tolerate it, go for the extra roommate.

Be sure to factor in management complexity, market research, and your risk tolerance as you evaluate options.Without a W-2, HELOC approval can be tricky, but some lenders will work with retired individuals, mainly if you can document stable income (rental income, retirement funds, etc.).

Many investors start with personal ownership and transfer the property to an LLC later, but it depends on your long-term goals and risk tolerance.

This will depend on your risk tolerance and your goals but you should consider starting with a single-family home to gain experience as a landlord and build your network.