Your thinking like an agent, and using agent perspective of how a brokerage should run.

Can run thousands.And while this isn't an "out of pocket" typically you will need some personal liquidity and net worth to secure loans.  

You'll need to run a proforma to figure out where these shake out for you!

. :)  How do you run the numbers on a PadSplit property?

Then, run a rental stress test on the new STR assuming a worst-case scenario—like converting it to a long-term rental with a 30% cut in future rents.

I run two big groups on fb and we have been bombarded by big pocket end buyers so closing big commercial deals 10M+ is not the challenge here. 

Things like landscaping/snow removal and labor cost for repairs are going to be highly variable based on your market so you'd need to do your own research on the going rate by either talking to other local investors, running your own google search, or exploring basic services on thumbtack/angies list etc. 

If you choose an area or decide to work with people who will take up more time due to the low cost of entry, you may end up paying more in the long run. 

This will help you in the long run, as you'll find your agent experience will be a blessing & a curse:- Blessing due to your understanding of MLS, searches & contracts.- Curse because MUST change your agent mindset.

Quote from @Matthew Brown: I run a small STR property management business.