Wow you are rockin! congrats on your new passion...
I used to play music up in Conrad and Shelby and Havre about 35 years ago (!), and love that area and especially the people!
My question is how Conrad is doing these days? I have no idea, but is it growing and does it have a good long term prognosis? That would be a good thing to figure in... because if it's declining, and if the young folks are moveing to bigger towns cities, etc, sometimes it can be a gamble in the long term hold idea. A lot of American small towns are dwindling...
Whereas, if you've got buyers for the flips, you may want to cash in on that, and potentially look at other places that do have good long term economies and are attracting millenials or short term rental people for the buy and hold...
Also, there seem to be some very good advantages to being a 'real estate professional' I think it's called: you have to work 750 hours per year on your real estate business (which you probably do, working on the houses--physically, and if you're managing them, marketing, leasing etc), and check with your accountant, but I think you get some pretty good tax advantages...
DEFINITELY go to the meet up in Havre... you can learn so much, and it's much easier and faster to convey information verbally instead of typing!! And listen to EVERY BP podcast!! I"m not kidding, they cover everything at one point or another. Ive been doing this a long time, and learn something new pretty much every podcast sometimes earthshattering stuff!... So while you're making those long montana drives, 0R PAINTING! listen to as much as you can
When you're figuring your cash flow, BE RUTHLESS! I"m too optimistic, so my wife holds my feet to fire... Figure 10% of gross income for repairs and maintenance, and create that reserve account for that. Talk to folks at meetups, other landlords in Conrad, shelby, and Havre and find out how long they're going between renters... and how much you spend in between renters on 'make ready'-- cleaning, painting, etc... That should be additional reserve; I think I figurre 10% vacancy, that includes lease up fees, and 'make ready' costs...
I"ll bet one good thing about Conrad is tenants probably stay long in a nice place!! that's good as Gold!
If there are any decent property managers there, Bug them for information, and find out how much they charge to manage properties (should be between 7% and 10%) and how much a lease up fee is... Figure this into your numbers, and if you manage it yourself, pay that to yourself, and THEN figure cashflow... because someday you may decide you don't want to manage them anymore, especially if they're not in your town.
Do you pay any of the utilities? You have to be crazy analytical on that stuff... I find that I pretty much spend 45% of my gross income on all the expenses, BEFORE mortgage payments...
That $150 may go away quickly, when you figure all that in, but If the market is appreciating really well, like better than 5%- 8%, losing a little monthly is worth it in the long run, if your regular income can easily cover it.
Good luck!