<prompt> Human: First post. Be gentle please. I am aware of all my mistakes and am here to learn.I reside in a suburb of Phoenix, AZ, alone with two dogs. Just closed my biz, looking for job in Operations Management. Pay is about 40k in current market. Very versatile set of skills, great attitude and very adaptable. No degree. Side hustle for extra cash on craigslist, will continue to do so once working.Goal: build savings and develop a solid retirement plan.I have seen Roth IRAs mentioned here quite a bit so I plan on putting my next 5500 there. Once I obtain a job I will save as much as possible and Id like to have a plan in place so I can start immediately once that occurs. My current home is near big sporting events, a large university, tourist areas, etc.; I have upgraded it over the years and have a few DIY projects going so I was thinking of buying a small home 100k to move into while fixing it up myself and renting out my current home as a vacation rental, which will bring in enough money to cover the mortgage and expenses at both houses. I am concerned about having expenses at both places however, if during the hot summer months it isnt consistently rented. I will not be selling my current home as it is really the only place Ive ever called home and am leaving it to my child. Im open to the financial wizards out there willing to share your thoughts.My financial info:House - paid 60k worth 250kSavings - 4kEmergency cash - 4kLife insurance - 250k if I outlive the policy at age 68, it pays 31k that I plan on investingCredit cards - 0Monthly expenses - 1,600 paid through July. This includes all utilities, internet, homeautolife insurance, property taxes, security alarm, cell phone, termite warranty, auto registration and a small food budget.FICO- 835TLDR: 50f No financial plan. No idea where to start.Edit: for some reason line breaks show on my end but not when posted. My apologies.  <response>: Buying another house sounds like a terrible idea. It is totally undiversified and illiquid. You may have extended periods without tenants. Unless you have retirement accounts you didnt mention, that should be your top priority once you land a job. Dont worry about what you may or may not leave to your kid. Getting a housemate sounds like a great idea. I agree with the pp that age discrimination is a real thing. You dont say what your experience is. I wouldnt hold out too long waiting for the perfect job. It is easier to find a better job if you have one. 