Upfront expenses and monthly payments must be considered when calculating the return on your investment.EXAMPLEI will provide details below, but here's the short version for those who hate to read or do math.

Anyone been in a similar situation or is able to provide any insight?

From their site on disputing reviews:Reviews should be relevantReviews must provide relevant information about the reviewer’s experience with the Host, guest, stay, or Experience that would help other community members make informed booking and hosting decisions.

YES replace the roof, about 250- 275  a sq depending on pitch.

I had given them the cost segregation studies for both properties that were provided to me but they didn't use them. 

Tenant laws depend by regions, but in general it's a bad idea to accept partial payments as there is a chance you need to wait longer for evictions.

I understand that I should have a separate bank account from my personal checking/savings, but based on my research, this first deal won't necessarily provide cashflow with me living in one of the units (it will when I move out).

If the property does not provide for all three, you should not underwrite or make investment decisions based on the property operating as an STR.

Seems like there has to be options that are relatively low(er) risk and can provide a foot in to start growing funds.Here are some possible budgets and I'd love your input on how you would start out at some or each of these price points:$10K, 20K, 30K, 40K, 50K, 60K.

Correct me if I am wrong.What services is the accountant providing you and what communications are you looking for.Does the $900 already include filing of a tax return and bookkeeping?