Don't know how to start. Please help break these two options down

[Brandon Reed]

Hi BP,

My wife and I are new to RE investing and are looking to get started using the "house hacking" strategy. We're already approved for a conventional loan and have the funds for a down payment that would be enough for either of these properties (below).

We like the potential in both of these options but are completely paralyzed with what to do next. I don't even really know where to begin with what information you'd need in order to provide insight to us.

We'll obviously live in one of the units and rent the other out. Do we just look at something like rentometer.com to get an idea of what rental rates are in these areas? Then once we know what we could get for them monthly, how do we start with calculating ALL the other pieces with what expenses will be, accounting for vacancy, maintenance, etc. There are SO many things we could estimate and we feel really overwhelmed. When looking at a potential deal are you supposed to make sure ALL of those pieces are estimated really confidently? Or is just recommended that you have a certain few really solid and the rest aren't really needed....?

Deal #1 would need to be rehabbed much more than Deal #2, which we are fine with. We actually may prefer that just because it would give us the experience. Deal #2 is currently being used for a vacation rental and is very consistently booked. We'd consider continuing to rent the 2nd unit as a vacation rental if the numbers made sense for the time we'd have to put into that. Deal #1 would be long term tenants. Regardless of the property, we'd probably move out within around 12 months or so and begin renting out the unit we were living in. Both areas are nice and are only getting nicer. Both areas have several other flips we've seen.

So I honestly don't even really know what questions to ask. I've spent the last 6 months or so digging in heavily to books, podcasts, attending my local REI, etc. It's just that when it comes time for rubber to meet the road I'm having a really hard time applying all I've learned to actual specific deals in my area. And you hear 10 different strategies for every approach so all of those are spinning through my mind when I look at deals and I don't know which one to actually implement/when ones will actually be helpful and effective.

Honestly any insight you can give us on how/where to start would be so appreciated and helpful! Also, if you would be able to give your opinion on if either of the deals looks like a good option for what we are trying to do, we would be so thankful for that as well.

Thank you so much in advance for any time you can give us.

Deal #1: 8 Broad Street, Winter Garden, FL 34787 - https://www.trulia.com/property/1061556577-8-Broad...

Deal #2: 412 Desoto Street, Clermont, FL 34711 - https://www.trulia.com/property/3241875418-412-W-D...