. - I have an STR here in Chicago and the only reason I keep the STR is because I have been grandfathered in since it's been over 5 years.In all honesty, you are better off doing a long term rental then trying to mess with a short term property in Chicago these days. 

Good luck to all 100% agree my folks I fund in Cleveland put new roofs on all new mechanicals update plumbing new electrical if needed I mean a true rehab.. not just patch..

If I’m buying a STR property now, what do I have to keep in mind if I also plan on buying a primary residence next year?

If you are renting keep in mind tenant will beat it up so don't overdue it

And if the house isn't currently selling at the price you've set... that means the appraisal may come in lower too. 1 - Doesn't matter much at this scale of the business.

You have 60k, are adding 12k per year, and want to keep 30k in reserves.

I understand that, but if you keep it as a primary residence and do some sort of house hacking deal where you rent out rooms, can you get passed that?

That will keep them coming back and they will bring their contacts.

Still, some exist so keep your wallet at home for these.

@Daniel TorresWhen you mention “investors” that plural means in most instances you would need to file for a sec exemption unless it’s one investor for one deal (or in CA can do trust deeds).It’s up to you whether you offer debt or equity.