The post below has a link to it if you’re curious:https://www.biggerpockets.com/topics/693527It was my attempt to model the key financial incentives for REI, which members have mentioned above, like inflation protection, capital appreciation, tax benefits, equity build up, and of course the beauty of refinancing.If you’re familiar with project financing you’ll know as value of real capital appreciates regearing will boost returns quite significantly.

The biggest reason I have the umbrella is for exactly that reason. 

Not an uncommon situation, and depending on the exact details there are still some community lending incentives you could have as a first-time borrower to help with the costs. 

Excellent communication can make or break a relationship.Tenant Screening Process:One of the biggest headaches for landlords is problem tenants, and a good property manager should have a thorough screening process in place.

The best thing to do would be to consult an attorney, but likely, that is not an option for everyone starting out.I'm not an attorney, and this is not legal advice, but some of the information that we include in our contracts is:- A clear scope of work - Payment schedule / Milestones- Change order approval process- Allowances for finished materials- Reasons to terminate the contract- Expectations for start date (X amount of time after final plans /permits are received or X amount of time after the contract is executed)- General schedule and timeline (This is where you could specify an end date - however it may be better use incentives rather than liquidated damage if your general contractor is late - we've done both, but found General Contractors respond better to getting something if they get done early instead of being punished for being late. 

I would say the biggest factor though would be scalability.

Hello all,I have been contemplating getting a vacation rental but biggest issue would be financing.

(we created a construction rescue program as a result of this) We provide excellent incentives for our investors,including locking in long term debt at 3.75 % through our in-house financing program. 2 years free property management as well.

My biggest issue was the lack of communication which we discussed.

You got some great advice above from @Nathan Gesner and @Rene Hosman, so I will keep it short.My biggest piece of advice is to get involved in some of the local Chicago meetups.