Newsflash: Currently have 3 properties, looking for a plan. Any advice is appreciated.

I’m a 30 year old married guy with a few homes and hoping to get some advice from you guys. I’m in IT for a university, my wife is a speech pathologist for a university. She loves her job, and I like mine too, but I dont want to be doing it forever. She most likely does. I want to ‘retire’ before I’m 40, meaning doing real estate/property management as my sole source of income and less than 40 hours a week.Property 1SFH – 2br 1.5ba 2car attached garage Purchased in 2010 for $68000 – Mortgage – 20% down 15 year at a rate of 3.25. Owe roughly $40k currently Current comps in the area are around $110k-$125k Monthly payment is $580 with taxes included, rented at $1050 Property 2SFH – 3br 1.5ba 2car attached garage Purchased in 2011 for $75000 Mortgage – 20% down 15 year at a rate of 3.75. Owe roughly 45k~ Current comps in the area are around $120k-150k Monthly payment is $680 with taxes included, rented at $1140 Property 3SFH – Primary residence – 2 br 2.5 ba condo Purchased in 2014 for $275000 Mortgage – 25% down 30 year at 3.9. Owe $195k~ Appraised at $325k before repairs. Comps in the area are around $315-360k. Redid kitchen, floors, opened kitchen area, redid one of the bathrooms Monthly payment is about $1950 including HOA, taxes, parking fee. Eventually we plan to move from the city and my original plan was to rent this property. Comparable rents in the area are $2800-$3500Personal assets – roughly 30k in cash, 80k invested, 25k in a RothIRAIf I don’t do anything else, I’ll have property 1 and 2 paid off by the time Im 40. We’ll be able to buy our next home with cash in the next few years. Rent out property 3, and I should have a rough net income of $2500-3000~ or so. Our next home (property 4) wouldnt have a mortgage, so personal expenses won’t be that high. However, I’d like to do more…I’d like to get another property, either another SFH in the same city as prop 1 and 2. Or alternatively, I’d like to get a vacation rental in a nearby city from 1 and 2, and about 2 hours from where I currently live. I have experience with AirBnB and would like to VRBO/Airbnb the vacation rental. I feel like vacation rentals would be the fastest way for me to make this a lifestyle business and quit my dayjob.The vacation rental I wont be able to pay cash for, and would need to secure financing to purchase it. I’ve found some waterfront properties around $150-$250k, the lower end requiring about $20-30k to get them vacation rentable, and about $5k for the higher end.I could most likely find a decent SFH that I could pay cash for through an LLC and renovate. Prices are higher than 5 years ago, but I feel fairly confident I could get something similar to property 1 and 2 for 80k, and put about 5-10k into it. I’d then rent it, have it appraised, and hopefully secure a mortgage at a decent rate. Then, hopefully repeat that process.If I want to eventually acquire 2-5 more properties in the next 10 years, should I refinance any of my current mortgages to get more liquid cash to work with? Would it make sense to refinance one of my properties to buy a vacation rental with cash?I’d love help with a strategy, or a better opinion of ‘here’s what I would do in your situation’



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