Maybe rents have not been raised in years; you maybe can get rents higher in line with the market.

On the other hand the advice to buy every 18 months, hack and move leaving a tenant behind, is a good strategy, if you can not raise the down payment. 

Loooong story short, my HOA: Can't afford to make the repairAre getting bids to fix the roofHaven't fixed it or done anything about it yet (it's now March 11th)Will probably ask for a special assessment in the near future and/or raise our duesThey have no real timeline for the repair and "thank me for my patience." 

Bonus for you, it's completely passive -- we do all the work and send you the returns.Here's how it works -- we find an apartment complex, get it under contract, get a loan, raise money from private investors for down payment and rehab costs, then manage the property and renovations... 

I get the cancellation fears but I find it interesting my group booked 8 days ago then night before raise concerns?

What is better the long game or raise the rent and possibly lose what I think are the perfect tenants?

The tenants in the 2BR/2Ba unit asked if I was planning to raise rents and when I said yes, they said they would look for a new place and ended up finding a place to break their lease early too.

It's a messed up system, tenants want their rent to stay really low, so they don't report problems, and always pay on time.. landlord is happy because not costing extra.. meanwhile the house goes downhill, and the next buyer is the one dealing with the issues fixing years of problems.. and then you raise rent, and the tenants hate you as the new big bad landlord who is greedy! 

your best bet in entrepreneurship is toA) build an A teamB) pursue an A/B ideaC) raise moneyso start networking and keep an eye outfor a business partner with income/credit :)

In this scenario, my 2020 AGI will be approximately 25,000 and after standard deduction, my taxable income will be approximately 0, and I still have no federal income tax liability for 2020.Follow on question is, can i claim "active participation" for one tax year (2019), and switch to claim NOT "active participation" the next year (2020) and hope this does not raise any ire with IRS, and is good tax planning.