Advice for the next potential purchase

[Victoria Gambardella]

The first goal I want to achieve is getting my living expenses (Mortgage, HOA, Taxes, Insurance) completely paid for by others. My strategy: I'm fairly new to the Vermont area and there is always a factor of me potentially moving away for work, so I'm not 100% sure where I will be over the long haul. Any properties I look at I make sure that there are multiple exit strategies, it's easy to maintain / upkeep from a distance (in my area multifamilies are out for me due to high maintenance and inventory that is in really rough shape plus a crack down on local government for upkeep), and is strong on cash flow in some shape or form with the strategy being buy and hold.

I'm currently paying far too much in rent so I started to look this summer for a town home that I could live in and also get roommates. I found a perfect layout town home: 3 floors, at least 1 bedroom on every floor, at least 1 bathroom on every floor so it really is a perfect setup for roommates but it's a sizable investment 299k. That being said comparable in the same community are 320k and selling within 24-48 hours on the market this is a FSBO so I got a heads up on it. Roommates would bring in 1700 with me also living on the property. The deal stalled as the property had some work being done on it.

In the meantime I found a small condo 5 min walk to the lake for a really inexpensive price - 2 br 1 bath 169k. I bought it and spent 30 days fixing it up in 3 weeks I had 3 prospective tenants. It's rented cash flow positive for $500 a month (even with mortgage, hoa etc.). It's my very first property and I'm quite thrilled with it (p.s. I also got an offer for 30k above what I bought it for but my strategy is buy and hold). Approximately 3 months after that rented - I got a call that the original deal is back on the table as all work was complete. If I successfully rent to roommates I will have achieved my goal of zeroing out my expenses but be pretty out of the market for approximately 2-3 years while I re-establish my savings. I'm looking for advice and watch outs on my  thinking from other investors since I'm so new to the market on the investing side. 

Property specifics: 

- Turn Key

- Can be sold quickly 24-48 hours (hot market for the past 3-5 years with housing shortage)

- Can be rented down the road for cash flow positive return $200-$300 per month if need be

- Roommates would be attracted to it but I could also afford to live there on my own if I absolutely had to (but it's far too much house for one person and I would be far away from achieving my original goal if that was the case)

Happy to provide any more details.