Maybe I’m being a little optimistic, but I feel like this is a good starting point for us.I’m not interested in investing outside of Orange County for our first property since we know the area really well.Networking:I’d also love to attend some real estate meetups around here and connect with people in the space.

I also agree that RE appreciation is unlikely to match the last dozen years, but you never know.Where I am unsure we agree is that paying $450k to improve the cash flow ~$3k (your numbers but I expect my delta wold be similar meaning both my cash flow estimates would be worse than yours but both would be worse by the same amount not affecting the difference) makes sense especially if the cost of having the extra $450k is only 6% rate which is historically simple to beat via numerous investment options and hopefully no one is investing in RE for an expected of 6%.  

I haven't had opportunity to attend yet. 

I hadn't read the Baltimore story before...wow.Hi Sathiya, some thoughts: - attend in person meet ups in the Boston area to talk to other investors who buy locally and out of state to get their feedback and maybe consider looking within a 2 to 3 hour drive. - cash flow is difficult now with long term rentals even if you pick markets that have lower purchase prices than Boston.

Search the BP for ADU appraisals to encounter numerous examples.

I faced numerous hurdles and stressful moments, but I persevered and built a successful approach.To tackle this challenge, I recommend starting early by building relationships and seeking investors.

@Diana Teng there are a LOT of potential pitfalls:(So, it's vitaly important to not just find someone that you think you can trust because they tell you what you want to hear, but you find someone that their processes seem a good fit for what you want.EXAMPLE: we do BRRR Turnkeys for clients and take numerous vides we share with them - initial, worst state of any demo, when HVAC, plumbing, electrical update BEFORE walled in, before any major payouts and of course a final walk-thru video.One thing that's accurate from all the HGTV renovation/flip shows is that you should expect and plan for surprises!

My question is: how do you do that and comply with Dodd Frank, which imposes numerous regulations if you finance more than 3 properties per year to consumers who will reside in those properties?  

I would recommend finding some local meetups to attend, and also tuning into the Straight Up Chicago Investor's Podcast.

Attend meet-ups.